Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters

Review Chemistry, Multidisciplinary

Single-electron transfer oxidation-induced C-H bond functionalization via photo-/ electrochemistry

Lijun Lu et al.

Summary: C-H bond functionalization, a hot topic in synthetic chemistry, allows the construction of compounds under mild conditions and holds great potential for various applications.

TRENDS IN CHEMISTRY (2022)

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Article Chemistry, Organic

Cu-Catalyzed Oxidative Thioesterification of Aroylhydrazides with Disulfides

Shimin Xie et al.

Summary: The alternative thioesterification reaction developed in this study utilizes readily available aroylhydrazides and disulfides, producing various thioesters in good to excellent yields with good functional group tolerance. The reaction mechanism involves tandem processes including deprotonation, free-radical-mediated denitrogenation, and C-S bond formation facilitated by the reaction of copper salt and oxidant (NH4)(2)S2O8.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Organic

Electroreductive C3 Pyridylation of Quinoxalin-2(1H)-ones: An Effective Way to Access Bidentate Nitrogen Ligands

Jiangwei Wen et al.

Summary: The electroreductive-induced C3 pyridylation of quinoxalin-2(1H)-ones with cyanopyridines provides a convenient, efficient, and gram-scale synthesis strategy for a series of new types of potential bidentate nitrogen ligands, achieving yields of over 95% in more than 36 examples.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Selective Electrochemical Oxidation of Functionalized Pyrrolidines

Nicholas R. Deprez et al.

Summary: This study presents an effective method for the selective oxidation of pyrrolidines to pyrrolidinones, showing high selectivity and functional group compatibility. It demonstrates the use of an operationally simple ElectraSyn 2.0 and cost-effective stainless-steel electrode for this electrochemical oxidation process.

ORGANIC LETTERS (2021)

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Article Chemistry, Organic

Reductive Arylation of Aliphatic and Aromatic Aldehydes with Cyanoarenes by Electrolysis for the Synthesis of Alcohols

Xiao Zhang et al.

Summary: An electroreductive arylation reaction of aliphatic and aromatic aldehydes as well as ketones with electro-deficient (hetero)arenes is described, providing secondary and tertiary alcohols in moderate to good yields. Mechanistic studies support the generation of aliphatic ketyl radicals and persistent heteroaryl radical anions via cathodic reduction followed by radical-radical cross-coupling.

ORGANIC LETTERS (2021)

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Article Chemistry, Applied

Isocyanide-Induced Esterification of Sulfinic Acids to Access Sulfinates

Jianjing Yang et al.

Summary: An isocyanide-induced esterification of sulfinic acids with alcohols or thiophenols to access sulfinates has been developed. The method showed advantages of simple operation, good functional group tolerance, and up to 99% yields in over 40 examples.

ADVANCED SYNTHESIS & CATALYSIS (2021)

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Article Chemistry, Organic

Hydrosilane-Mediated Electrochemical Reduction of Amides

Kazuhiro Okamoto et al.

Summary: The electrochemical reduction of amides was achieved using a hydrosilane without toxic or expensive metals. The key reactive ketyl radical intermediate was generated through cathodic reduction, leading to chemoselective deoxygenation to produce corresponding amines with anodically generated silyl radicals or zinc bromide.

JOURNAL OF ORGANIC CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative radical cascade cyclization of olefinic amides and thiophenols towards the synthesis of sulfurated benzoxazines, oxazolines and iminoisobenzofurans

Fangling Lu et al.

Summary: A new electrochemical oxidative strategy was introduced to construct heterocycles containing N and O without the need for a transition-metal catalyst and an external oxidant. Various olefinic amides and thiophenols/diselenides were reacted in a simple undivided cell to produce thiolation and selenylation heterocycles in up to 83% yields, providing a facile method for constructing C-S/C-Se and C-O bonds in one step.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Scalable electrochemical reduction of sulfoxides to sulfides

Zhenshuo Kong et al.

Summary: This report introduces a scalable electrochemical reduction of sulfoxides using a substoichiometric amount of Lewis acid AlCl3, which can be regenerated through an inexpensive aluminum anode with chloride anion. The process features a broad substrate scope, including acid-labile substrates and drug molecules.

GREEN CHEMISTRY (2021)

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Article Chemistry, Multidisciplinary

Electrochemical oxidative thiocyanation and amination of enaminones towards the synthesis of multi-substituted alkenes

Fangling Lu et al.

Summary: A highly stereoselective synthesis of thiocyanated enaminones was achieved through an electrochemical process, with up to 87% yields. The transformation proceeded smoothly without the need for external oxidants, electrolytes, or transition-metal catalysts, showcasing its potential for practical application.

GREEN CHEMISTRY (2021)

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Review Chemistry, Multidisciplinary

Methods for the direct synthesis of thioesters from aldehydes: a focus review

Noor H. Jabarullah et al.

JOURNAL OF SULFUR CHEMISTRY (2020)

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Article Chemistry, Multidisciplinary

Efficient electrosynthesis of sulfinic esters via oxidative cross-coupling between alcohols and thiophenols

Fengping Gong et al.

JOURNAL OF THE CHINESE CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides

Ke-Jin Jiao et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Multidisciplinary

Direct and Scalable Electroreduction of Triphenylphosphine Oxide to Triphenylphosphine

Shuhei Manabe et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Electrochemical Synthesis of Hindered Primary and Secondary Amines via Proton-Coupled Electron Transfer

Dan Lehnherr et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Organic

Thioesterification and Selenoesterification of Amides via Selective N-C Cleavage at Room Temperature: N-C(O) to S/Se-C(O) Interconversion

Md Mahbubur Rahman et al.

SYNTHESIS-STUTTGART (2020)

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Article Chemistry, Multidisciplinary

Electroreductive Cobalt-Catalyzed Carboxylation: Cross-Electrophile Electrocoupling with Atmospheric CO2

Nate W. J. Ang et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

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Article Chemistry, Physical

Photocatalytic Deoxygenation of Sulfoxides Using Visible Light: Mechanistic Investigations and Synthetic Applications

Aimee K. Clarke et al.

ACS CATALYSIS (2020)

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Article Chemistry, Organic

Electrochemical Oxidative Phosphorylation of Aldehyde Hydrazones

Zhongnan Xu et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Organic

Nickel-Catalyzed Reductive Aryl Thiocarbonylation of Alkene via Thioester Group Transfer Strategy

Yunxia Feng et al.

ORGANIC LETTERS (2020)

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Article Chemistry, Inorganic & Nuclear

A novel approach toward thioester bond formation mediated byN,N'-diisopropylcarbodiimide in water

Nadia Fattahi et al.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (2020)

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Article Chemistry, Multidisciplinary

An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond

Lingxiang Lu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Article Chemistry, Multidisciplinary

Electroreductive Olefin-Ketone Coupling

Pengfei Hu et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2020)

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Review Chemistry, Multidisciplinary

Electrifying green synthesis: recent advances in electrochemical annulation reactions

Guilherme M. Martins et al.

GREEN CHEMISTRY (2020)

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Article Multidisciplinary Sciences

Scalable and safe synthetic organic electroreduction inspired by Li-ion battery chemistry

Byron K. Peters et al.

SCIENCE (2019)

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Article Chemistry, Organic

Visible-Light-Promoted Thiyl Radical Generation from Sodium Sulfinates: A Radical-Radical Coupling to Thioesters

Ganganna Bogonda et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Physical

Enantioselective Electroreductive Coupling of Alkenyl and Benzyl Halides via Nickel Catalysis

Travis J. DeLano et al.

ACS CATALYSIS (2019)

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Article Chemistry, Organic

Electrochemical Dehydrogenative Phosphorylation of Alcohols for the Synthesis of Organophosphinates

Lingling Deng et al.

JOURNAL OF ORGANIC CHEMISTRY (2019)

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Article Chemistry, Organic

Fukuyama Cross-Coupling Approach to Isoprekinamycin: Discovery of the Highly Active and Bench-Stable Palladium Precatalyst POxAP

Shuang-Qi Tang et al.

ORGANIC LETTERS (2019)

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Article Chemistry, Multidisciplinary

Electrochemical benzylic oxidation of C-H bonds

Jason A. Marko et al.

CHEMICAL COMMUNICATIONS (2019)

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Article Chemistry, Multidisciplinary

Decarbonylative thioetherification by nickel catalysis using air- and moisture-stable nickel precatalysts

Chengwei Liu et al.

CHEMICAL COMMUNICATIONS (2018)

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Review Chemistry, Multidisciplinary

Miniaturization and Combinatorial Approach in Organic Electrochemistry

Koichi Mitsudo et al.

CHEMICAL REVIEWS (2018)

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Article Chemistry, Multidisciplinary

Electrochemical C-H Cyanation of Electron-Rich (Hetero)Arenes

Davit Hayrapetyan et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Review Chemistry, Multidisciplinary

Metal-Catalyzed Synthesis and Use of Thioesters: Recent Developments

Vera Hirschbeck et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Article Chemistry, Multidisciplinary

Electroremovable Traceless Hydrazides for Cobalt-Catalyzed Electro-Oxidative C-H/N-H Activation with Internal Alkynes

Ruhuai Mei et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2018)

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Article Chemistry, Organic

Bromide-catalyzed electrochemical trifluoromethylation/cyclization of N-arylacrylamides with low catalyst loading

Yang-Ye Jiang et al.

ORGANIC CHEMISTRY FRONTIERS (2018)

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Article Chemistry, Multidisciplinary

Electrochemical Synthesis of 5-Aryl-phenanthridin-6-one by Dehydrogenative N,C Bond Formation

Anton Kehl et al.

CHEMISTRY-A EUROPEAN JOURNAL (2018)

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Review Chemistry, Multidisciplinary

Use of Electrochemistry in the Synthesis of Heterocyclic Structures

Yangye Jiang et al.

CHEMICAL REVIEWS (2018)

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Article Chemistry, Organic

Highly Active Manganese-Mediated Acylation of Alcohols with Acid Chlorides or Anhydrides

Seong-Ryu Joo et al.

SYNLETT (2017)

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Article Chemistry, Organic

A synthesis of biaryl ketones via the C-S bond cleavage of thiol ester by a Cu/Ag salt

Prasanjit Ghosh et al.

TETRAHEDRON LETTERS (2017)

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Article Chemistry, Organic

Harnessing the catalytic behaviour of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP): An expeditious synthesis of thioesters

Pallavi Singh et al.

TETRAHEDRON LETTERS (2017)

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Article Chemistry, Multidisciplinary

Thioesters synthesis: recent adventures in the esterification of thiols

Mosstafa Kazemi et al.

JOURNAL OF SULFUR CHEMISTRY (2015)

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Article Chemistry, Multidisciplinary

Aldehyde Capture Ligation for Synthesis of Native Peptide Bonds

Monika Raj et al.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2015)

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Article Chemistry, Organic

Catalyst-free direct decarboxylative coupling of α-keto acids with thiols: a facile access to thioesters

Kelu Yan et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2015)

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Article Chemistry, Organic

Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

Chunhuan He et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2014)

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Article Chemistry, Organic

Tris(pentafluorophenyl)borane catalyzed acylation of alcohols, phenols, amines, and thiophenols under solvent-free condition

Santosh Kumar Prajapti et al.

TETRAHEDRON LETTERS (2014)

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Article Chemistry, Applied

Tetraethylammonium Bromide-Catalyzed Oxidative Thioesterification of Aldehydes and Alcohols

Xuebin Zhu et al.

ADVANCED SYNTHESIS & CATALYSIS (2013)

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Article Chemistry, Inorganic & Nuclear

AN EFFICIENT SYNTHESIS OF THIOESTERS VIA TFA-CATALYZED REACTION OF CARBOXYLIC ACID AND THIOLS: REMARKABLY FACILE C-S BOND FORMATION

Adel S. El-Azab et al.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (2012)

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Article Chemistry, Multidisciplinary

Synthesis of Acylsilanes by Palladium-catalyzed Cross-coupling Reaction of Thiol Esters and Silylzinc Chlorides

Hiroki Azuma et al.

CHEMISTRY LETTERS (2011)

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Article Chemistry, Organic

Zn in ionic liquid: an efficient reaction media for the synthesis of diorganyl chalcogenides and chalcogenoesters

Senthil Narayanaperumal et al.

TETRAHEDRON (2011)

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Article Chemistry, Multidisciplinary

Organic electrosynthesis: a promising green methodology in organic chemistry

Bernardo A. Frontana-Uribe et al.

GREEN CHEMISTRY (2010)

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Article Chemistry, Organic

Efficient copper-catalyzed coupling of aryl iodides and thiobenzoic acid

Naotaka Sawada et al.

TETRAHEDRON LETTERS (2006)

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Article Chemistry, Applied

Ionic liquid as catalyst and reaction medium: A simple, convenient and green procedure for the synthesis of thioethers, thioesters and dithianes using an inexpensive ionic liquid, [pmIm]Br

BC Ranu et al.

ADVANCED SYNTHESIS & CATALYSIS (2005)

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Review Chemistry, Multidisciplinary

Organoselenium and organotellurium compounds: Toxicology and pharmacology

CW Nogueira et al.

CHEMICAL REVIEWS (2004)

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Review Biochemistry & Molecular Biology

Palmitoylation of intracellular signaling proteins: Regulation and function

JE Smotrys et al.

ANNUAL REVIEW OF BIOCHEMISTRY (2004)

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Article Chemistry, Inorganic & Nuclear

Deoxygenation of sulfoxides to thioethers by molybdenum pentachloride (MoCl5) and reductive coupling of sulfonyl chlorides to disulfides

H Firouzabadi et al.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS (2001)

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Article Chemistry, Organic

An efficient synthetic route to aryl thiocyanates from arenesulfinates

IWJ Still et al.

SYNTHETIC COMMUNICATIONS (2001)

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Review Biochemistry & Molecular Biology

Polyketide biosynthesis: a millennium review

J Staunton et al.

NATURAL PRODUCT REPORTS (2001)

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Electrochemical reductive cross-coupling of acyl chlorides and sulfinic acids towards the synthesis of thioesters

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