Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach

Article Chemistry, Multidisciplinary

Radical Carbonyl Umpolung Arylation via Dual Nickel Catalysis

Huan-Ming Huang et al.

Summary: This study discloses a reverse strategy to achieve radical carbonyl arylation via dual catalysis, which can construct complex organic compounds without the need for pre-functionalization.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Article Chemistry, Multidisciplinary

Site-Selective Pyridylic C-H Functionalization by Photocatalytic Radical Cascades

Myojeong Kim et al.

Summary: An efficient method for functionalizing pyridines and quinolines through radical-mediated reactions has been developed, allowing for selective modification of heteroatom positions.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Review Chemistry, Multidisciplinary

N-Functionalized Pyridinium Salts: A New Chapter for Site-Selective Pyridine C-H Functionalization via Radical-Based Processes under Visible Light Irradiation

Myojeong Kim et al.

Summary: This article provides a comprehensive overview of the development of N-functionalized pyridinium salts and summarizes the cornerstones of organic reactions that successfully employ these pyridinium salts under visible light conditions. Major advances in the field are systematically categorized based on the pyridines' N-substituent, N-X (X = O, N, C, and SO2CF3), and its reactivity patterns.

ACCOUNTS OF CHEMICAL RESEARCH (2022)

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Article Chemistry, Multidisciplinary

Site-Selective Pyridine C-H Alkylation with Alcohols and Thiols via Single-Electron Transfer of Frustrated Lewis Pairs

Chang-Yin Tan et al.

Summary: A unified strategy for the deoxygenative or desulfurative pyridylation of various alcohols and thiols has been developed using a single-electron transfer (SET) process mediated by frustrated Lewis pairs (FLPs). The method involves the formation of FLPs between pyridinium salts and PtBu3, and the generation of alkyl radicals through the ionic coupling of phosphine radical cations with in situ generated xanthates. Visible-light irradiation enhances the reaction efficiency. This method offers a previously unrecognized opportunity for the selective heteroarylation of alcohols and thiols with diverse functional groups.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2022)

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Article Chemistry, Physical

Photocatalytic Decarboxylative Pyridylation of Carboxylic Acids Using In Situ-Generated Amidyl Radicals as Oxidants

Changha Kim et al.

Summary: A highly efficient visible-light-mediated C-H alkylation of pyridines at the C4 position using alkyl carboxylic acids as alkylating agents is reported in this study. The released N-centered radical acts as an effective oxidizing agent for single-electron transfer (SET) oxidation to regenerate the photocatalyst, making this photocatalytic system appealing from a mechanistic perspective. The strategy offers a practical approach for the C4-selective pyridylation of carboxylic acids and amino acids with various functional groups under mild, metal-free conditions.

ACS CATALYSIS (2022)

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Article Chemistry, Multidisciplinary

Diversification of Unprotected Alicyclic Amines by C-H Bond Functionalization: Decarboxylative Alkylation of Transient Imines

Anirudra Paul et al.

Summary: Despite efforts by practitioners, direct alpha-C-H bond functionalization of unprotected alicyclic amines is rare. A new method utilizing N-lithiated alicyclic amines has been developed, providing a convenient approach to achieve functionalization reactions under mild conditions. This method offers a new pathway for the synthesis of beta-amino ketones with regioselective alpha'-alkylation, and potential for one-pot synthesis of polycyclic dihydroquinolones.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Visible-Light-Induced 1,3-Aminopyridylation of [1.1.1]Propellane with N-Aminopyridinium Salts

Sanghoon Shin et al.

Summary: The formation of an electron donor-acceptor complex allowed for the direct installation of amino and pyridyl groups onto bicyclo[1.1.1]pentane (BCP) frameworks in the absence of an external photocatalyst. This method is robust and metal-free, enabling late-stage modification of structurally complex biorelevant molecules. The strategy also facilitates the incorporation of functional groups with pyridine across the BCP core, significantly expanding the range of potential applications for drug discovery.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

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Article Chemistry, Multidisciplinary

Site-Selective Direct C-H Pyridylation of Unactivated Alkanes by Triplet Excited Anthraquinone

Wooseok Lee et al.

Summary: A novel modular photochemical platform for site-selective C-H pyridylation of unactivated hydrocarbons in chemical feedstocks has been developed, allowing for direct construction of high-value-added compounds under ambient reaction conditions. The system shows high levels of site selectivity and is applicable to a variety of linear-, branched-, and cyclo-alkanes as well as more complex molecules under visible-light conditions.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2021)

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Review Chemistry, Multidisciplinary

Advances in N-centered intermediates by energy transfer photocatalysis

Milan Bera et al.

Summary: Advances in visible-light-mediated EnT catalysis have enabled a unique strategy for small-molecule activation and new chemical bond formation in organic synthesis. Open-shell nitrogen reactive intermediates have emerged as versatile synthons for various cross-coupling reactions and the construction of N-heterocycles through visible-light-induced EnT catalysis.

TRENDS IN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Divergent reactivity of sulfinates with pyridinium salts based on one- versus two-electron pathways

Myojeong Kim et al.

Summary: The modern synthesis aims to develop distinct reaction pathways from identical starting materials for efficient synthesis of diverse compounds. By controlling the reaction conditions and using specific compound combinations, the method allows for high-efficiency synthesis of a variety of compounds with a broad substrate scope and mild reaction conditions.

CHEMICAL SCIENCE (2021)

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Review Chemistry, Multidisciplinary

Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes

Giacomo E. M. Crisenza et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Multidisciplinary

When Light Meets Nitrogen-Centered Radicals: From Reagents to Catalysts

Xiao-Ye Yu et al.

ACCOUNTS OF CHEMICAL RESEARCH (2020)

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Article Chemistry, Multidisciplinary

CuII/TEMPO-Catalyzed Enantioselective C(sp3)-H Alkynylation of Tertiary Cyclic Amines through Shono-Type Oxidation

Pei-Sen Gao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Physical

B(C6F5)3-Catalyzed Direct C3 Alkylation of Indoles and Oxindoles

Shyam Basak et al.

ACS CATALYSIS (2020)

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Article Chemistry, Physical

Regioselective Cross-Electrophile Coupling of Epoxides and (Hetero)aryl Iodides via Ni/Ti/Photoredox Catalysis

Marvin Parasram et al.

ACS CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Highly Diastereoselective Functionalization of Piperidines by Photoredox-Catalyzed α-Amino C-H Arylation and Epimerization

Morgan M. Walker et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Rapid functionalization of multiple C-H bonds in unprotected alicyclic amines

Weijie Chen et al.

NATURE CHEMISTRY (2020)

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Article Chemistry, Applied

Formal Ring Contraction of Cyclic N-Sulfonamides via C-N Bond Cleavage and α-Amination by Oxidation of Halides

Yuna Nishiguchi et al.

ADVANCED SYNTHESIS & CATALYSIS (2020)

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Article Chemistry, Multidisciplinary

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

Sungwoo Jung et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Ruthenium-Catalyzed Hydrogen Evolution o-Aminoalkylation of Phenols with Cyclic Amines

Liang Cao et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

B(C6F5)3-Catalyzed β-Functionalization of Pyrrolidines Using Isatins via Borrowing Hydrogen: Divergent Access to Substituted Pyrrolidines and Pyrroles

Yong Chen et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Visible-Light-Mediated C-H Alkylation of Pyridine Derivatives

Fatima Rammal et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Functionalization of Pyridinium Derivatives with 1,4-Dihydropyridines Enabled by Photoinduced Charge Transfer

Inwon Kim et al.

ORGANIC LETTERS (2020)

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Article Multidisciplinary Sciences

Ring-opening functionalizations of unstrained cyclic amines enabled by difluorocarbene transfer

Youyoung Kim et al.

NATURE COMMUNICATIONS (2020)

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Article Chemistry, Multidisciplinary

Deconstructive Functionalizations of Unstrained Carbon-Nitrogen Cleavage Enabled by Difluorocarbene

Jianke Su et al.

ACS CENTRAL SCIENCE (2020)

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Article Chemistry, Physical

Photochemical C-H Silylation and Hydroxymethylation of Pyridines and Related Structures: Synthetic Scope and Mechanisms

Fatima Rammal et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Solvent-Regulated Coupling of 2-Alkynylbenzaldehydes with Cyclic Amines: Selective Synthesis of Fused N-Heterocycles and Functionalized Naphthalene Derivatives

Yan He et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Multidisciplinary

α-Functionalization of Cyclic Secondary Amines: Lewis Acid Promoted Addition of Organometallics to Transient Imines

Anirudra Paul et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2019)

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Article Chemistry, Multidisciplinary

Direct Arylation of α-Amino C(sp3)-H Bonds by Convergent Paired Electrolysis

Yueyue Ma et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2019)

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Article Chemistry, Organic

Redox-Neutral β-C(sp3)-H Functionalization of Cyclic Amines via Intermolecular Hydride Transfer

Lan Zhou et al.

ORGANIC LETTERS (2019)

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Article Multidisciplinary Sciences

Visible light induced alkene aminopyridylation using N-aminopyridinium salts as bifunctional reagents

Yonghoon Moon et al.

NATURE COMMUNICATIONS (2019)

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Article Chemistry, Organic

Visible-light-mediated -phosphorylation of N-aryl tertiary amines through the formation of electron-donor-acceptor complexes: synthetic and mechanistic studies

Valentin Quint et al.

ORGANIC CHEMISTRY FRONTIERS (2019)

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Article Chemistry, Multidisciplinary

Direct α-C-H bond functionalization of unprotected cyclic amines

Weijie Chen et al.

NATURE CHEMISTRY (2018)

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Generation and Alkylation of alpha-Carbamyl Radicals via Organic Photoredox Catalysis

Joshua B. McManus et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Electrochemical Acceptorless Dehydrogenation of N-Heterocycles Utilizing TEMPO as Organo-Electrocatalyst

Yong Wu et al.

ACS CATALYSIS (2018)

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Photoinduced Deaminative Borylation of Alkylamines

Jingjing Wu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Electrochemical Aminoxyl-Mediated alpha-Cyanation of Secondary Piperidines for Pharmaceutical Building Block Diversification

Alastair J. J. Lennox et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Deconstructive fluorination of cyclic amines by carbon-carbon cleavage

Jose B. Roque et al.

SCIENCE (2018)

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Visible-Light-Induced Pyridylation of Remote C(sp3)-H Bonds by Radical Translocation of N-Alkoxypyridinium Salts

Inwon Kim et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Dehydrogenative Aromatization and Sulfonylation of Pyrrolidines: Orthogonal Reactivity in Photoredox Catalysis

Krishnamoorthy Muralirajan et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2018)

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Deaminative Borylation of Aliphatic Amines Enabled by Visible Light Excitation of an Electron Donor-Acceptor Complex

Frederik Sandfort et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Catalytic Access to Bridged Sila-N-heterocycles from Piperidines via Cascade sp(3) and sp(2) C-Si Bond Formation

Jianbo Zhang et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Deconstructive diversification of cyclic amines

Jose B. Roque et al.

NATURE (2018)

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One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade ,-sp3 C-H bond difunctionalization and C-N bond cleavage

Kaixuan He et al.

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Visible light photoredox-controlled reactions of N-radicals and radical ions

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Metal-Free, Visible Light-Photocatalyzed Synthesis of Benzo[b]phosphole Oxides: Synthetic and Mechanistic Investigations

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C-H functionalization of amines with aryl halides by nickel-photoredox catalysis

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Organic Synthesis Enabled by Light-Irradiation of EDA Complexes: Theoretical Background and Synthetic Applications

Carolina G. S. Lima et al.

ACS CATALYSIS (2016)

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The Azomethine Ylide Route to Amine C-H Functionalization: Redox-Versions of Classic Reactions and a Pathway to New Transformations

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ACCOUNTS OF CHEMICAL RESEARCH (2015)

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Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis

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Rings in Drugs

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JOURNAL OF MEDICINAL CHEMISTRY (2014)

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Iron-Catalyzed Oxidative C(3)-H Functionalization of Amines

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Platinum-Catalyzed Michael Addition and Cyclization of Tertiary Amines with Nitroolefins by Dehydrogenation of α,β-sp3 C-H Bonds

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Direct sp3 C-H bond activation adjacent to nitrogen in heterocycles

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Deconstructive Pyridylation of Unstrained Cyclic Amines through a One-Pot Umpolung Approach

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