Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Iodine‐catalyzed C−H functionalization has emerged as an attractive tool for the construction of various C−X (X=C, N, O, S, etc.) bonds, without the use of toxic transition‐metal catalysts. Nevertheless, strong chemical oxidants are usually required for the regeneration of iodine‐containing catalysts, which leads to poor atom economy and undesirable side reactions. Organic electrochemistry provides new opportunities for the assembly of various chemical bonds in an environmentally friendly manner. This Minireview discusses the recent advances of synthetic electrochemistry in C−H functionalization with various iodine‐containing reagents.

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Recent Advances in C−H Functionalization with Electrochemistry and Various Iodine‐Containing Reagents

Qian

Zha

Wang

2020

ChemElectroChem

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Oxo‐Thiolation of Cationically Polymerizable Alkenes Using Flow Microreactors

Ashikari

Saito

Nokami

et al. 2019

Chemistry A European J

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Electrochemical Cross‐Dehydrogenative Coupling between Phenols and β‐Dicarbonyl Compounds: Facile Construction of Benzofurans

Wang

Tian

Ding

et al. 2020

Chemistry A European J

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Preparative electrochemical synthesis is an ideal method for establishing green, sustainable processes. The major benefits of an electro‐organic strategy over that of conventional chemical synthesis are the avoidance of reagent waste and mild reaction conditions. Here, an intermolecular cross‐dehydrogenative coupling between phenols and β‐dicarbonyl compounds has been developed to build various benzofurans under undivided electrolytic conditions. Neither transition metals nor external chemical oxidants are required to facilitate the dehydrogenation and dehydration processes. The key factor in success was the use of nBu4NBF4 as the electrolyte and hexafluoroisopropanol as the solvent, which play key roles in the cyclocondensation step. This electrolysis is scalable and can be used as a key step in drug synthesis. On the basis of several experimental results, the mechanism, particularly of the remarkable anodic oxidation and cyclization process, was illustrated.

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Metal‐ and Oxidant‐Free Alkenyl C−H/Aromatic C−H Cross‐Coupling Using Electrochemically Generated Iodosulfonium Ions

Cited by 8 publications

References 64 publications

Recent Advances in C−H Functionalization with Electrochemistry and Various Iodine‐Containing Reagents

Recent Advances in C−H Functionalization with Electrochemistry and Various Iodine‐Containing Reagents

Oxo‐Thiolation of Cationically Polymerizable Alkenes Using Flow Microreactors

Electrochemical Cross‐Dehydrogenative Coupling between Phenols and β‐Dicarbonyl Compounds: Facile Construction of Benzofurans

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