☆ 4.7 Review

CH-Functionalization of Heterocycles with the Formation of C-O, C-N, C-S/Se, and C-P Bonds by Intermolecular Addition of Heteroatom-Centered Radicals

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Metal-Free Direct Oxidative C-N Bond Coupling of Quinoxalin-2(1H)-ones with Azoles under Mild Conditions

Jingwen Guo et al.

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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

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Sulfenylation of Indoles Mediated by Iodine and Its Compounds

Olga M. Mulina et al.

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Mn-Catalyzed Electrooxidative Undirected C-H/P-H Cross-Coupling between Aromatics and Diphenyl Phosphine Oxides

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Visible Light-Driven and Singlet Oxygen-Mediated Photochemical Cross-Dehydrogenative C3-H Sulfenylation of 4-Hydroxycoumarins with Thiols Using Rose Bengal as a Photosensitizer

Goutam Brahmachari et al.

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JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Wansoo Kim et al.

Summary: The oxidation potential-guided electrochemical radical-radical cross-coupling reactions provide a simple and direct synthetic route to 3-sulfonylated imidazopyridines and indolizines, showcasing the green synthetic nature of the reactions without the need for oxidants or metals.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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B(C6F5)3-Catalyzed Electron Donor-Acceptor Complex-Mediated Aerobic Sulfenylation of Indoles under Visible-Light Conditions

Wenkai Yuan et al.

Summary: An efficient aerobic oxidative C-S cross-coupling reaction of thiophenol with indoles was developed using B(C6F5)(3) as a single-electron oxidant, producing a wide range of diaryl sulfides in good yields. The formation of an electron donor-acceptor complex between B(C6F5)(3) and indoles facilitated the photoinduced single-electron transfer from indole substrates to the B(C6F5)(3) catalyst. This protocol demonstrates a new reaction model for oxidative C-S cross-coupling reactions.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Copper-catalyzed C-H Selenation of 2-Substituted Benzo[b]furans with Diaryl Diselenides: Synthesis of 2-Substituted 3-Selanylbenzo[b]furan Derivatives

Yuki Murata et al.

Summary: A novel method for the synthesis of 2-substituted 3-selanylbenzo[b]furans using Cu-catalyzed C-H selenation was developed in this study. The reaction proceeds efficiently and the yields of the corresponding compounds range from moderate to excellent. This method offers a convenient and effective way to transform aromatic heterocycles.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Metal-free electrochemical [3+2] heteroannulation of anilines with pyridines enabled by dual C-H radical aminations

Mu-Jia Luo et al.

Summary: This method describes an unprecedented metal-/external-oxidant-free electrochemical intermolecular [3 + 2] heteroannulation of anilines with electron-deficient pyridines enabled by dual C-H radical aminations for producing functionally diverse benzo[4,5]imidazo[1,2-a]pyridines. The site-selectivity of aminations of aryl C(sp(2))-H bonds relies on the electronic effect of two reaction partners, with electron-withdrawing groups at the 4 position of the pyridine ring being crucial. Mechanistic studies show that the method sequence involves the generation of the nitrogen-centered radical (NCR), the pyridine radical anion, radical coupling, and dual C-N aminations.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Electro-oxidative C-H amination of heteroarenes with aniline derivatives via radical-radical cross coupling

Xichao Peng et al.

Summary: The study proposes a sustainable method for the selective synthesis of C-2/C-3 aminated five-membered heteroarenes incorporated with functionalities from aniline derivatives through an electro-oxidative cross coupling process. This approach enables the synthesis of a wide variety of heteroarene derivatives, tolerates functional groups, and is suitable for gram-scale synthesis. Preliminary mechanistic studies suggest a radical cross coupling process between the N-centered radical and indole radical cation may be involved in this amination reaction.

GREEN CHEMISTRY (2021)

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Article Chemistry, Organic

Electrochemical sulfonylation of imidazoheterocycles under batch and continuous flow conditions

Elise Leclercq et al.

Summary: An efficient and versatile protocol for the C-H sulfonylation of imidazoheterocycles via electrochemical activation was established, showing selective functionalization under catalyst- and oxidant-free conditions and tolerance to various functional groups. The reaction proceeded successfully with various sodium sulfinates and a range of imidazoheterocycles, with significantly accelerated and higher yields achieved under microfluidic conditions.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

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Review Materials Science, Multidisciplinary

Indole fused heterocycles as sensitizers in dye-sensitized solar cells: an overview

P. R. Nitha et al.

Summary: Extensive research has been conducted in the past three decades on developing non-metallic organic dyes for dye sensitized solar cells (DSSCs). Organic dyes have emerged as the most promising candidate for DSSCs due to their performance, easy synthesis, stability, low cost, and eco-friendly characteristics. Indole fused heterocycles have found wide applications as sensitizers in DSSCs, offering stability, ease of synthesis, and preventing sensitizer aggregation.

MATERIALS ADVANCES (2021)

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Article Chemistry, Multidisciplinary

A radical-mediated multicomponent cascade reaction for the synthesis of azide-biindole derivatives

Xiaoyu Liu et al.

Summary: A new radical-mediated, one-pot, multicomponent cascade reaction was developed for the synthesis of azide-biindole derivatives. Mechanistic studies showed the formation of nitrogen-centred free radicals which initiated the cascade reaction to obtain the final products. This methodology may have potential applications in constructing other azido heterocycles.

CHEMICAL COMMUNICATIONS (2021)

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Embedding CsPbBr3 quantum dots into a pillar[5]arene-based supramolecular self-assembly for an efficient photocatalytic cross-coupling hydrogen evolution reaction

Kaipeng Zhong et al.

Summary: The study successfully fabricated a highly efficient artificial light-harvesting system by embedding CsPbBr3 quantum dots into a supramolecular self-assembly, demonstrating excellent photocatalytic activity and significantly increased product yield. This research paves a new way for utilizing perovskite quantum dots to construct efficient light-harvesting systems for solar energy conversion.

JOURNAL OF MATERIALS CHEMISTRY A (2021)

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Article Chemistry, Multidisciplinary

Metal free C-3 chalcogenation (sulfenylation and selenylation) of 4H-pyrido[1,2-a]pyrimidin-4-ones

Prasanjit Ghosh et al.

Summary: An expeditious metal-free synthesis method has been developed for synthesizing diverse 3-ArS/ArSe derivatives with high yields (up to 95%) of 4H-pyrido[1,2-a]pyrimidin-4-one. This operationally simple reaction, conducted under mild conditions, can be scaled up to gram quantities and shows broad functional group tolerance. Preliminary experimental investigations suggest a radical mechanistic pathway for these transformations.

RSC ADVANCES (2021)

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Article Chemistry, Multidisciplinary

Electrochemical synthesis of versatile ammonium oxides under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions

Yong Yuan et al.

Summary: An electrochemical oxidative cross-coupling reaction has been developed, producing a series of unprecedented cross-coupling products under metal catalyst-, exogenous-oxidant-, and exogenous-electrolyte-free conditions. The resulting products are nearly insoluble in solvent, allowing for pure product isolation without silica gel column purification, and the prepared ammonium oxides are versatile building blocks for synthesizing pyrazole derivatives.

CHEMICAL COMMUNICATIONS (2021)

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Article Chemistry, Organic

Electrochemical Oxidative C-H Thiocyanation or Selenocyanation of Imidazopyridines and Arenes

Ting Cui et al.

Summary: Regioselective electrochemical oxidative C-H thiocyanation or selenocyanation of imidazopyridines was achieved using an undivided electrolytic cell, under transition-metal- and oxidant-free conditions. A library of thiocyanated imidazopyridines with a broad range of functional groups were synthesized in high yields. This method was also applicable to the thiocyanation or selenocyanation of some electron-rich arenes.

SYNLETT (2021)

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Article Chemistry, Organic

N-(Alkoxy)- and N-(acyloxy)phthalimides in organic synthesis: free radical synthetic approaches and applications (microreview)

Alexander S. Budnikov et al.

CHEMISTRY OF HETEROCYCLIC COMPOUNDS (2020)

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Article Chemistry, Organic

Metal-Free Direct C-H Thiolation and Thiocyanation of Pyrazolones

Tanakorn Kittikool et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Regioselective C-H Sulfonylation of 2H-Indazoles by Electrosynthesis

Kingshuk Mahanty et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

δ-C-H Mono- and Dihalogenation of Alcohols

Alastair N. Herron et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

PhI(OAc)2-mediated oxidative C-H sulfoximination of imidazopyridines under mild conditions

Nannan Luan et al.

TETRAHEDRON LETTERS (2020)

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Review Chemistry, Applied

Recent Progress in the Construction of C-N Bonds via Metal-Free Radical C(sp3)-H Functionalization

Si-Zhe Song et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Organic

Photocatalytic Synthesis of 3-Sulfanyl- and 1,3-Bis(sulfanyl)indolizines Mediated by Visible Light

Filipe Penteado et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Site-Selective Thiolation of (Multi)halogenated Heteroarenes

Frederik Sandfort et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Selective Oxidative Cleavage of 3-Methylindoles with Primary Amines Affording Quinazolinones

Junhui He et al.

ORGANIC LETTERS (2020)

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Review Chemistry, Organic

Oxime radicals: generation, properties and application in organic synthesis

Igor B. Krylov et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Silver-Catalyzed Remote C5-H Selenylation of Indoles

Wei-Hong Song et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Organic

Organophotoredox-Catalyzed Direct C-H Amination of 2H-Indazoles with Amines

Sukanya Neogi et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Electrochemical Radical-Radical Cross-Coupling Approach between Sodium Sulfinates and 2H-Indazoles to 3-Sulfonylated 2H-Indazoles

Wansoo Kim et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Iodine-Promoted Synthesis of 4-Aryl-2-(arylsulfonyl)quinolones by Desulfurative C-S Cross-Coupling Reaction of Quinoline-2-thiones with Sodium Sulfinates

Guo-Chao Yang et al.

SYNLETT (2020)

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Article Chemistry, Organic

Hydrogen Peroxide-Mediated Rapid Room Temperature Metal-Free C(sp2)-H Thiocyanation of Amino Pyrazoles, Amino Uracils, and Enamines

Danish Ali et al.

JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

C-H functionalization reactions enabled by hydrogen atom transfer to carbon-centered radicals

Sumon Sarkar et al.

CHEMICAL SCIENCE (2020)

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Review Chemistry, Multidisciplinary

Prescribed drugs containing nitrogen heterocycles: an overview

Majid M. Heravi et al.

RSC ADVANCES (2020)

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Article Chemistry, Organic

Three-Component C-H Bond Sulfonylation of Imidazoheterocycles by Visible-Light Organophotoredox Catalysis

Chloe Breton-Patient et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1H)-ones under aerobic metal-free conditions

Deepa Rawat et al.

GREEN CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Regioselective C-H sulfenylation ofN-sulfonyl protected 7-azaindoles promoted by TBAI: a rapid synthesis of 3-thio-7-azaindoles

Jingyan Hu et al.

RSC ADVANCES (2020)

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Article Chemistry, Multidisciplinary

Visible-light-induced ligand-free RuCl3 catalyzed C-H phosphorylation in water

Xue-Ya Gou et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Peroxidation of 3,4-dihydro-1,4-benzoxazin-2-ones

Jie Wang et al.

CHEMICAL COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Metal-free regioselective C-H chalcogenylation of coumarins/(hetero)arenes at ambient temperature

Zengqiang Song et al.

CHEMICAL COMMUNICATIONS (2020)

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Review Chemistry, Organic

Recent trends in catalytic sp3 C-H functionalization of heterocycles

Milanpreet Kaur et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2020)

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Article Chemistry, Organic

K2S2O8-promoted direct thiocyanation of pyrazolin-5-ones with ammonium thiocyanate at room temperature

Xiaokang Mao et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

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Review Chemistry, Multidisciplinary

Recent Advances in Minisci-Type Reactions

Rupert S. J. Proctor et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Selective Photocatalysis Approach for Introducing ArS Units into BODIPYs through Thiyl Radicals

Fangtao Ma et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Electrochemical oxidative selenylation of imidazo[1,2-a]pyridines with diselenides

Yeon Joo Kim et al.

TETRAHEDRON LETTERS (2019)

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Kharasch reaction: Cu-catalyzed and non-Kharasch metal-free peroxidation of barbituric acids

Oleg V. Bityukov et al.

TETRAHEDRON LETTERS (2019)

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Article Chemistry, Multidisciplinary

Mild Nitration of Pyrazolin-5-ones by a Combination of Fe(NO3)3 and NaNO2: Discovery of a New Readily Available Class of Fungicides, 4-Nitropyrazolin-5-ones

Igor B. Krylov et al.

CHEMISTRY-A EUROPEAN JOURNAL (2019)

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Article Chemistry, Organic

Metal-Free and Visible-Light-Promoted C-3 Thiocyanation of 2-Arylquinolin-4-ones

Parul Chauhan et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Metal-free cross-dehydrogenative C-N coupling of azoles with xanthenes and related activated arylmethylenes

Yanni Li et al.

SYNTHETIC COMMUNICATIONS (2019)

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Article Chemistry, Organic

Copper-Mediated Direct and Selective C-H Thiolation of Quinazolinones

Writhabrata Sarkar et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Applied

PIDA-Promoted Selective C5 C-H Selenylations of Indolines via Weak Interactions

Linghui Gu et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Applied

Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)-S/Se Bond Formation

Lu-Shan Huang et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Organic

Transition-Metal and Solvent-Free Oxidative C-H Fluoroalkoxylation of Quinoxalinones with Fluoroalkyl Alcohols

Jun Xu et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Synthesis of 3,3-Spirocyclic 2-Phosphonoindolines via a Dearomative Addition of Phosphonyl Radicals to Indoles

Dmytro Ryzhakov et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Organic

Direct C3 Alkoxylation of Quinoxalin-2(1H)-ones with Alcohols via Cross-Dehydrogenative Coupling under Catalyst-Free Conditions

Qiming Yang et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Review Chemistry, Multidisciplinary

Chemistry with Electrochemically Generated N-Centered Radicals

Peng Xiong et al.

ACCOUNTS OF CHEMICAL RESEARCH (2019)

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Article Chemistry, Organic

A Mild and Direct C(sp3)-S Cross-Coupling of Oxindoles with Thiols: Synthesis of Unsymmetrical 3-Thiooxindoles

Hui Qin et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Editorial Material Biochemistry & Molecular Biology

Heterocycles in Medicinal Chemistry

Josef Jampilek

MOLECULES (2019)

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Review Chemistry, Organic

Radical-Mediated Difunctionalization of Styrenes

Xiazhen Bao et al.

SYNTHESIS-STUTTGART (2019)

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Article Chemistry, Applied

Potassium Persulfate-Mediated Thiocyanation of 2H-Indazole under Iron-Catalysis

Amrita Dey et al.

ADVANCED SYNTHESIS & CATALYSIS (2019)

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Article Chemistry, Medicinal

Alkyl Sulfinates: Radical Precursors Enabling Drug Discovery

Joel M. Smith et al.

JOURNAL OF MEDICINAL CHEMISTRY (2019)

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Electrochemical Reductive Smiles Rearrangement for C-N Bond Formation

Xihao Chang et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Physical

Silver-Mediated Indole (4+2) Dearomative Annulation with N-Radicals: A Strategy To Construct Heterocycle-Fused Indolines

Lin-Bao Zhang et al.

ACS CATALYSIS (2019)

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Review Chemistry, Organic

Late stage functionalization of heterocycles using hypervalent iodine(iii) reagents

Rajnish Budhwan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Article Chemistry, Organic

Metal-free regioselective direct thiolation of 2-pyridones

Kunita Phakdeeyothin et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative C-H/N-H cross-coupling for C-N bond formation with hydrogen evolution

Yi Yu et al.

CHEMICAL COMMUNICATIONS (2019)

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Transition-metal-free regioselective cross-coupling of BODIPYs with thiols

Fan Lv et al.

CHEMICAL COMMUNICATIONS (2019)

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A metal- and oxidizing- reagent- free anodic para- selective amination of anilines with phenothiazines

Yan-Chen Wu et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Visible- light- induced metal and reagent- free oxidative coupling of sp2 C- H bonds with organodichalcogenides: synthesis of 3-organochalcogenyl indoles

Vandana Rathore et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Exogenous-oxidant- and catalyst-free electrochemical deoxygenative C2 sulfonylation of quinoline N-oxides

Minbao Jiang et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Recent advances in alkoxy radical-promoted C-C and C-H bond functionalization starting from free alcohols

Xinxin Wu et al.

CHEMICAL COMMUNICATIONS (2019)

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Review Chemistry, Multidisciplinary

Pharmacological significance of heterocyclic 1H-benzimidazole scaffolds: a review

Sumit Tahlan et al.

BMC CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Direct C-H sulfenylation of quinoxalinones with thiols under visible-light-induced photocatalyst-free conditions

Qing-Hu Teng et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Metal- and photocatalyst-free synthesis of 3-selenylindoles and asymmetric diarylselenides promoted by visible light

Ignacio D. Lemir et al.

RSC ADVANCES (2019)

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Article Chemistry, Multidisciplinary

Visible-light-induced deoxygenative C2-sulfonylation of quinoline N-oxides with sulfinic acids

Long-Yong Xie et al.

GREEN CHEMISTRY (2019)

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Article Chemistry, Multidisciplinary

Electrochemically enabled chemoselective sulfonylation and hydrazination of indoles

Yu-Zhen Zhang et al.

GREEN CHEMISTRY (2019)

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Alkoxy radicals generation: facile photocatalytic reduction of N-alkoxyazinium or azolium salts

Luca Capaldo et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Organic

Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides

Yu-Jing Guo et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Multidisciplinary

Catalyst- and Reagent-Free Electrochemical Azole C-H Amination

Youai Qiu et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Inorganic & Nuclear

External oxidant-free cross-coupling: electrochemically induced aromatic C-H phosphonation of azoles with dialkyl-H-phosphonates under silver catalysis

E. O. Yurko et al.

DALTON TRANSACTIONS (2018)

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Article Chemistry, Organic

Iron-Catalyzed Batch/Continuous Flow C-H Functionalization Module for the Synthesis of Anticancer Peroxides

Moreshwar B. Chaudhari et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

AgSbF6-Mediated Selective Thiolation and Selenylation at C-4 Position of Isoquinolin-1(2H)-ones

You-Quan Zhu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Direct C4-H phosphonation of 8-hydroxyquinoline derivatives employing photoredox catalysis and silver catalysis

Xiaoxue Su et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

An organocatalyst bound -aminoalkyl radical intermediate for controlled aerobic oxidation of iminium ions

Abdul Motaleb et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Rose Bengal catalysed photo-induced selenylation of indoles, imidazoles and arenes: a metal free approach

Sumbal Saba et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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Article Chemistry, Organic

Transition-Metal-Free Regioselective Cross-Coupling: Controlled Synthesis of Mono- or Dithiolation Indolizines

Bin Li et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Organic

Temperature Controlled Selective C-S or C-C Bond Formation: Photocatalytic Sulfonylation versus Arylation of Unactivated Heterocycles Utilizing Aryl Sulfonyl Chlorides

Santosh K. Pagire et al.

ORGANIC LETTERS (2018)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative phosphorylation of azoles in the presence of silver catalysts

E. O. Yurko et al.

RUSSIAN CHEMICAL BULLETIN (2018)

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Article Chemistry, Organic

Direct sulfonylation of pyrazolones with sodium sulfinates catalyzed by TBAI in water

Li-Xia Li et al.

TETRAHEDRON LETTERS (2018)

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Article Chemistry, Multidisciplinary

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

Xing Zhang et al.

RSC ADVANCES (2018)

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Review Chemistry, Organic

Visible-Light-Induced C-H Functionalization and C-C/C-X Bond-Forming Oxidative Cross-Coupling Reactions

Heng Zhang et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Applied

Radical C-H-Amination of Heteroarenes using Dual Initiation by Visible Light and Iodine

Nicola Lucchetti et al.

ADVANCED SYNTHESIS & CATALYSIS (2018)

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Article Chemistry, Multidisciplinary

Exogenous-oxidant-free electrochemical oxidative C-H sulfonylation of arenes/heteroarenes with hydrogen evolution

Yong Yuan et al.

CHEMICAL COMMUNICATIONS (2018)

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Article Chemistry, Organic

Copper-Catalyzed C5-H Sulfenylation of Unprotected 8-Aminoquinolines Using Sulfonyl Hydrazides

Qing Yu et al.

JOURNAL OF ORGANIC CHEMISTRY (2018)

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Article Chemistry, Organic

Iodine-Promoted C(sp2)-H Thiolation of Maleimides with Dimethyl Sulfoxide and Thiols

Hong-Ru Tan et al.

SYNTHESIS-STUTTGART (2018)

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Article Chemistry, Organic

KIO3-Catalyzed C(sp2)-H Bond Selenylation/Sulfenylation of (Hetero)arenes: Synthesis of Chalcogenated (Hetero)arenes and their Evaluation for Anti-Alzheimer Activity

Janh Rodrigues et al.

ASIAN JOURNAL OF ORGANIC CHEMISTRY (2018)

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Metal-free deoxygenative sulfonylation of quinoline N-oxides with sodium sulfinates via a dual radical coupling process

Long-Yong Xie et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Site-Specific Oxidative C-H Chalcogenation of (Hetero)Aryl-Fused Cyclic Amines Enabled by Nanocobalt Oxides

Zhenda Tan et al.

ORGANIC LETTERS (2018)

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Transition-metal-free KI-catalyzed regioselective sulfenylation of 4-anilinocoumarins using Bunte salts

Guoqing Li et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

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The fast and efficient KI/H2O2 mediated 2-sulfonylation of indoles and N-methylpyrrole in water

Jun Zhang et al.

RSC ADVANCES (2018)

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Electrochemical Conversion of Phthaldianilides to Phthalazin-1,4-diones by Dehydrogenative N-N Bond Formation

Anton Kehl et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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K2S2O8-Promoted Direct C-H Phosphorylation of (Benzo)thiazoles

Weidong Lin et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Electrooxidative Metal-Free Dehydrogenative α-Sulfonylation of 1H-Indole with Sodium Sulfinates

Mei-Lin Feng et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Article Chemistry, Organic

Recent Advances in Radical Dioxygenation of Olefins

Raghunath Bag et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Recent Advances in Radical Difunctionalization of Simple Alkenes

Xing-Wang Lan et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2017)

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Visible light-induced C-H sulfenylation using sulfinic acids

Pengfei Sun et al.

GREEN CHEMISTRY (2017)

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Convenient KI-catalyzed regioselective synthesis of 2-sulfonylindoles using water as solvent

Hongjie Li et al.

NEW JOURNAL OF CHEMISTRY (2017)

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Visible-light-promoted selective C-H amination of heteroarenes with heteroaromatic amines under metal-free conditions

Supravat Samanta et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Article Chemistry, Organic

Iodine-catalyzed direct C-H thiolation of imidazo [1,5-a]quinolines for the synthesis of 3-sulfenylimidazo[1,5-a]quinolines

Song-Song Wu et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2017)

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Editorial Material Chemistry, Organic

Radicals in Action: A Festival of Radical Transformations

Samir Z. Zard

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Transition-Metal-Free Selective Oxidative C(sp3)-S/Se Coupling of Oxindoles, Tetralone, and Arylacetamides: Synthesis of Unsymmetrical Organochalcogenides

Ch. Durga Prasad et al.

ORGANIC LETTERS (2017)

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Article Chemistry, Organic

Cross-Dehydrogenative C-H Amination of Indoles under Aerobic Photo-oxidative Conditions

Tomoaki Yamaguchi et al.

ORGANIC LETTERS (2017)

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Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of Coumarin-3-carboxylic Acids

Minghao Li et al.

ORGANIC LETTERS (2017)

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Metal-Free Mediated C-3 Methylsulfanylation of Imidazo[1,2-a]-pyridines with Dimethyl Sulfoxide as a Methylsulfanylating Agent

Zhengkai Chen et al.

SYNLETT (2017)

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A Sulfonylation Reaction: Direct Synthesis of 2-Sulfonylindoles from Sulfonyl Hydrazides and Indoles

Rajjakfur Rahaman et al.

SYNLETT (2017)

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Review Chemistry, Organic

Recent Advances in Iminyl Radical Cyclizations

Mary M. Jackman et al.

SYNTHESIS-STUTTGART (2017)

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Review Chemistry, Organic

Recent Advances in Reactions of Heteroatom-Centered Radicals

Tsuyoshi Taniguchi

SYNTHESIS-STUTTGART (2017)

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Article Chemistry, Multidisciplinary

Photocatalytic direct C-S bond formation: facile access to 3-sulfenylindoles via metal-free C-3 sulfenylation of indoles with thiophenols

Wei Guo et al.

RSC ADVANCES (2017)

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Article Chemistry, Organic

DMSO-promoted regioselective synthesis of sulfenylated pyrazoles via a radical pathway

Pengfei Sun et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Article Chemistry, Organic

Copper- catalyzed C5-selective thio/selenocyanation of 8-aminoquinolines

Jichao Chen et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Article Chemistry, Organic

Merging photoredox catalysis with transition metal catalysis: site-selective C4 or C5-H phosphonation of 8-aminoquinoline amides

Huijie Qiao et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Article Chemistry, Organic

Selective cross-dehydrogenative C-O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesis

Igor B. Krylov et al.

ORGANIC CHEMISTRY FRONTIERS (2017)

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Article Chemistry, Multidisciplinary

Copper-Catalyzed Remote C-H Sulfonylation of 8-Aminoquinoline Amides with Arylsulfonyl Hydrazides

Guoshu Chen et al.

CHEMISTRYSELECT (2017)

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Catalytic Dehydrogenative C-H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide

Eri Ito et al.

CHEM (2017)

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Review Chemistry, Inorganic & Nuclear

Boron-containing radical species

Yuanting Su et al.

COORDINATION CHEMISTRY REVIEWS (2017)

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Review Chemistry, Multidisciplinary

Recent Advances in Radical C-H Activation/Radical Cross-Coupling

Hong Yi et al.

CHEMICAL REVIEWS (2017)

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Article Chemistry, Applied

Regioselective Direct C3-Phosphorylation of N-Sulfonylindoles under Mild Oxidative Conditions

Feng Su et al.

ADVANCED SYNTHESIS & CATALYSIS (2017)

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Article Chemistry, Organic

Photoredox catalyst-mediated direct regioselective phosphonylation of indoles

Zijian Zhao et al.

SYNTHETIC COMMUNICATIONS (2016)

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Article Chemistry, Applied

Silver-Catalyzed Direct Csp2-H Phosphorylation of Indoles Leading to Phosphoindoles

Wang-Bin Sun et al.

ADVANCED SYNTHESIS & CATALYSIS (2016)

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Radical C-H functionalization to construct heterocyclic compounds

Jin-Tao Yu et al.

CHEMICAL COMMUNICATIONS (2016)

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Metal-free C-H sulfonamidation of pyrroles by visible light photoredox catalysis

Andreas Uwe Meyer et al.

CHEMICAL COMMUNICATIONS (2016)

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Review Chemistry, Multidisciplinary

Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions

Paula Ruiz-Castillo et al.

CHEMICAL REVIEWS (2016)

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Silicon based radicals, radical ions, diradicals and diradicaloids

Kartik Chandra Mondal et al.

CHEMICAL SOCIETY REVIEWS (2016)

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Review Chemistry, Multidisciplinary

New amination strategies based on nitrogen-centered radical chemistry

Tao Xiong et al.

CHEMICAL SOCIETY REVIEWS (2016)

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Visible-Light-Induced Direct Oxidative C-H Amidation of Heteroarenes with Sulfonamides

Kun Tong et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

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Article Chemistry, Physical

N-heterocycles as corrosion inhibitors for mild steel in acid medium

Jagadeesan Saranya et al.

JOURNAL OF MOLECULAR LIQUIDS (2016)

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Autoxidative C(sp2)-P Formation: Direct Phosphorylation of Heteroarenes under Oxygen, Metal-Free, and Solvent-Free Conditions

Kai Luo et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Manganese(III) Acetate-Promoted Cross-Coupling Reaction of Benzothiazole/Thiazole Derivatives with Organophosphorus Compounds under Ball-Milling Conditions

Liang Li et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Article Chemistry, Organic

C-H Phosphonation of Pyrrolopyrimidines: Synthesis of Substituted 7-and 9-Deazapurine-8-phosphonate Derivatives

Nazarii Sabat et al.

JOURNAL OF ORGANIC CHEMISTRY (2016)

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Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition Metal-Free Hydroamination and N-Arylation Reactions

Jacob Davies et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Radicals: Reactive Intermediates with Translational Potential

Ming Yan et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2016)

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Review Biochemistry & Molecular Biology

Review Functionalised Oximes: Emergent Precursors for Carbon-, Nitrogen- and Oxygen-Centred Radicals

John C. Walton

MOLECULES (2016)

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Modern advances in heterocyclic chemistry in drug discovery

Alexandria P. Taylor et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2016)

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Cu-Catalyzed Deoxygenative C2-Sulfonylation Reaction of Quinoline N-Oxides with Sodium Sulfinate

Bingnan Du et al.

ORGANIC LETTERS (2016)

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Cross-Coupling Hydrogen Evolution by Visible Light Photocatalysis Toward C(sp2)-P Formation: Metal-Free C-H Functionalization of Thiazole Derivatives with Diarylphosphine Oxides

Kai Luo et al.

ORGANIC LETTERS (2016)

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Copper(II)-catalyzed remote sulfonylation of aminoquinolines with sodium sulfinates via radical coupling

Chengcai Xia et al.

RSC ADVANCES (2016)

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Silver(I)-promoted C5-H phosphonation of 8-aminoquinoline amides with H-phosphonates

Mengmeng Sun et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

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Visible light mediated aerobic radical C-H phosphorization toward arylphosphonates

Pan Peng et al.

ORGANIC CHEMISTRY FRONTIERS (2016)

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Detection of the Short-Lived Radical Cation Intermediate in the Electrooxidation of N,N-Dimethylaniline by Mass Spectrometry

Timothy A. Brown et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

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Cross-dehydrogenative coupling for the intermolecular C-O bond formation

Igor B. Krylov et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Silver-mediated direct phosphorylation of benzothiazoles and thiazoles with diarylphosphine oxides

Hui-Jun Zhang et al.

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Olefinic C-H functionalization through radical alkenylation

Shan Tang et al.

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Regioselective Oxidative C-H Phosphonation of Imidazo[1,2-a]pyridines and Related Heteroarenes Mediated by Manganese(III) Acetate

Mahipal Yadav et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2015)

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Metal-Free Thiocyanation of Imidazoheterocycles through Visible Light Photoredox Catalysis

Shubhanjan Mitra et al.

JOURNAL OF ORGANIC CHEMISTRY (2015)

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Photostabilizing Efficiency of PVC in the Presence of Schiff Bases as Photostabilizers

Emad Yousif et al.

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Difunctionalization of Acrylamides through C-H Oxidative Radical Coupling: New Approaches to Oxindoles

Ren-Jie Song et al.

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Recent advances in sulfur- and phosphorous-centered radical reactions for the formation of S-C and P-C bonds

Xiang-Qiang Pan et al.

TETRAHEDRON (2015)

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The development of carbene-stabilized N-O radical coupling strategy in metal-free regioselective C-H azidation of quinoline N-oxides

Pan Li et al.

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N-Aminopyridinium Salts as Precursors for N-Centered Radicals - Direct Amidation of Arenes and Heteroarenes

Tobias W. Greulich et al.

ORGANIC LETTERS (2015)

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Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles

Jia-Rong Chen et al.

SYNTHESIS-STUTTGART (2015)

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Radical C-H Functionalization of Heteroarenes under Electrochemical Control

Alexander G. O'Brien et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2014)

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Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis

Hyejin Kim et al.

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Selective sulfonylation and diazotization of indoles

Jiang-Kai Qiu et al.

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Thiyl Radicals in Organic Synthesis

Fabrice Denes et al.

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Visible-Light Promoted Catalyst-Free Imidation of Arenes and Heteroarenes

Lu Song et al.

CHEMISTRY-A EUROPEAN JOURNAL (2014)

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Regioselective C2 Sulfonylation of Indoles Mediated by Molecular Iodine

Praewpan Katrun et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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Peroxides as Switches of Dialkyl H-Phosphonate: Two Mild and Metal-Free Methods for Preparation of 2-Acylbenzothiazoles and Dialkyl Benzothiazol-2-ylphosphonates

Xiao-Lan Chen et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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A Visible-Light-Promoted Aerobic Metal-Free C-3 Thiocyanation of Indoles

Weigang Fan et al.

JOURNAL OF ORGANIC CHEMISTRY (2014)

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A Mild, Ferrocene-Catalyzed C-H Imidation of (Hetero)Arenes

Klement Foo et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2014)

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N-Acyloxyphthalimides as Nitrogen Radical Precursors in the Visible Light Photocatalyzed Room Temperature C-H Amination of Arenes and Heteroarenes

Laura J. Allen et al.

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Radical Addition to Iminium Ions and Cationic Heterocycles

Johannes Tauber et al.

MOLECULES (2014)

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Iodine-Catalyzed Regioselective 2-Sulfonylation of Indoles with Sodium Sulfinates

Fuhong Xiao et al.

ORGANIC LETTERS (2014)

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Visible-Light-Promoted Redox Neutral C-H Amidation of Heteroarenes with Hydroxylamine Derivatives

Qixue Qin et al.

ORGANIC LETTERS (2014)

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An expedient synthesis of pyrrole-2-phosphonates via direct oxidative phosphorylation and γ-hydroxy-γ-butyrolactams from pyrroles

Se Hee Kim et al.

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An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

Marcus Baumann et al.

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY (2013)

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Thiols, thioethers, and related compounds as sources of C-centred radicals

Fabrice Denes et al.

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Synthesis of Benzidine Derivatives via FeCl3•6H2O-Promoted Oxidative Coupling of Anilines

Xuege Ling et al.

JOURNAL OF ORGANIC CHEMISTRY (2013)

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I2/TBHP-Catalyzed Chemoselective Amination of Indoles

Zhong-Jian Cai et al.

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Heterocyclic chemistry in crop protection

Clemens Lamberth

PEST MANAGEMENT SCIENCE (2013)

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Mn(OAc)3-Mediated Selective Free Radical Phosphonylation of Pyridinones and Pyrimidinones

Wang-Bin Sun et al.

SYNTHESIS-STUTTGART (2013)

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An efficient synthesis of 5-phosphorylated uracil derivatives: oxidative cross-coupling between uracil and dialkyl phosphites

Se Hee Kim et al.

TETRAHEDRON LETTERS (2013)

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Carbene-stabilized main group radicals and radical ions

Caleb D. Martin et al.

CHEMICAL SCIENCE (2013)

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Cross Coupling of Acyl and Aminyl Radicals: Direct Synthesis of Amides Catalyzed by Bu4NI with TBHP as an Oxidant

Zhaojun Liu et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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C-H Bond Functionalization: Emerging Synthetic Tools for Natural Products and Pharmaceuticals

Junichiro Yamaguchi et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2012)

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Pd-Catalyzed Threefold Arylation of Baylis-Hillman Bromides and Acetates with Triarylbismuth Reagents

Maddali L. N. Rao et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2012)

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Coupling Reactions of Heteroarenes with Phosphites under Silver Catalysis

Chang-Bing Xiang et al.

JOURNAL OF ORGANIC CHEMISTRY (2012)

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Manganese(III) Acetate Mediated Free-Radical Phosphonylation of Flavones and Coumarins

Peng Zhou et al.

SYNTHESIS-STUTTGART (2012)

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Direct Oxidative C-P Bond Formation of Indoles with Dialkyl Phosphites

Haolong Wang et al.

SYNTHESIS-STUTTGART (2012)

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Recent developments in natural product synthesis using metal-catalysed C-H bond functionalisation

Lindsay McMurray et al.

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Minisci reactions: Versatile CH-functionalizations for medicinal chemists

Matthew A. J. Duncton

MEDCHEMCOMM (2011)

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Highly Efficient N-Heterocyclic Carbene/Pyridine-Based Ruthenium Sensitizers: Complexes for Dye-Sensitized Solar Cells

Wei-Chun Chang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2010)

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Manganese(III)-mediated direct phosphonylation of arenes

Wei Xu et al.

TETRAHEDRON LETTERS (2010)

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Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions

Florian Monnier et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2009)

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Recent progress in the generation and use of nitrogen-centred radicals

Samir Z. Zard

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Carbon-heteroatom bond formation catalysed by organometallic complexes

John F. Hartwig

NATURE (2008)

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Thiol-mediated radical cyclization: regioselective formation of indole-annulated sulfur heterocycles by tandem cyclization

K. C. Majumdar et al.

TETRAHEDRON LETTERS (2007)

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What's new in stable radical chemistry?

Robin G. Hicks

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Stretching bonds in main group element compounds - Borderlines between biradicals and closed-shell species

Frank Breher

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Chemical sensors based on amplifying fluorescent conjugated polymers

Samuel W. Thomas et al.

CHEMICAL REVIEWS (2007)

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Radical addition reactions of phosphorus hydrides: Tuning the reactivity of phosphorus hydrides, the use of microwaves and Horner-Wadsworth-Emmons-type reactions

CM Jessop et al.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY (2006)

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Recent advances in the use of phosphorus-centered radicals in organic chemistry

D Leca et al.

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Palladium-catalyzed C-N and C-O coupling - A practical guide from an industrial vantage point

B Schlummer et al.

ADVANCED SYNTHESIS & CATALYSIS (2004)

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Persistent and stable radicals of the heavier main group elements and related species

PP Power

CHEMICAL REVIEWS (2003)

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Selectivity in the chemistry of oxygen-centered radicals - The formation of carbon-oxygen bonds

J Hartung et al.

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