Conventional methods for carrying out carbon–hydrogen functionalization and carbon–nitrogen bond formation are typically conducted at elevated temperatures, and rely on expensive catalysts as well as the use of stoichiometric, and perhaps toxic, oxidants. In this regard, electrochemical synthesis has recently been recognized as a sustainable and scalable strategy for the construction of challenging carbon–carbon and carbon–heteroatom bonds. Here, electrosynthesis has proven to be an environmentally benign, highly effective and versatile platform for achieving a wide range of nonclassical bond disconnections via generation of radical intermediates under mild reaction conditions. This review provides an overview on the use of anodic electrochemical methods for expediting the development of carbon–hydrogen functionalization and carbon–nitrogen bond formation strategies. Emphasis is placed on methodology development and mechanistic insight and aims to provide inspiration for future synthetic applications in the field of electrosynthesis.

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Electrochemical strategies for C-H functionalization and C-N bond formation.

Hypervalent iodine reagents as a new entrance to organocatalysts

Arylated products are found in various fields of chemistry and represent essential entities for many applications. Therefore, the formation of this structural feature represents a central issue of contemporary organic synthesis. By the action of electricity the necessity of leaving groups, metal catalysts, stoichiometric oxidizers, or reducing agents can be omitted in part or even completely. The replacement of conventional reagents by sustainable electricity not only will be environmentally benign but also allows significant short cuts in electrochemical synthesis. In addition, this methodology can be considered as inherently safe. The current survey is organized in cathodic and anodic conversions as well as by the number of leaving groups being involved. In some electroconversions the reagents used are regenerated at the electrode, whereas in other electrotransformations free radical sequences are exploited to afford a highly sustainable process. The electrochemical formation of the aryl–substrate bond ...

Electrochemical Arylation Reaction.

Synthetic Applications of Anodic Electrochemistry

Cyclohexadienone ketals and quinols: four building blocks potentially useful for enantioselective synthesis.

Anodic oxidation of p-methoxy-substituted phenols and electron-rich styrene or propenylbenzene derivatives affords in good yield trans-dihydrobenzofurans derived from a formal 1,3-oxidative cycloaddition of the phenol to the styrene derivative. The yield of product in the electrochemical oxidation depends upon the ratio of phenol to styrene derivative, current density, and to a lesser extent the amount of supporting electrolyte

Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives

Oxidation of p-methoxy-substituted phenols with iodobenzene bis-trifluoroacetate in the presence of electron-rich styrene derivatives affords trans-dihydrobenzofurans stereoselectively

A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols

Total Synthesis of the Cembranoid Diterpene Lactone (+)-Cleomeolide. Some Remarkable Conformational Features of Nine-Membered Belts Linked in 2,6-Fashion to a Methylenecyclohexane Core

Efficient synthesis of vinyl ethers of spiroquinol ketals and their high-yield photochemical oxygen-to-carbon [1,3]-shift to spiro-fused 2,5-cyclohexadienones

La cinetique et des aspects mecanistiques de la transposition thermique d'arylidene-3 dihydro-1,3 spiro [benzo [c] pyranne-1:1'-cyclohexadiene-2,'5'one-4] en oxo-4 aryl-2' spiro [cyclohexadiene-2,5-1:1'-indanone-3'] ont ete etudies

Spiro-fused 2,5-cyclohexadienones from the thermal 1,3-alkyl migrations of quinol vinyl ethers. A strategy for conversion of a carbonyl carbon to a quaternary carbon

Shaopeng Wang

Papers

Mechanistic aspects and synthetic applications of the electrochemical and iodobenzene bistrifluoroacetate oxidative 1,3-cycloadditions of phenols and electron-rich styrene derivatives

A convergent route to dihydrobenzofuran neolignans via a formal 1,3-cycloaddition to oxidized phenols

Total Synthesis of the Cembranoid Diterpene Lactone (+)-Cleomeolide. Some Remarkable Conformational Features of Nine-Membered Belts Linked in 2,6-Fashion to a Methylenecyclohexane Core

Efficient synthesis of vinyl ethers of spiroquinol ketals and their high-yield photochemical oxygen-to-carbon [1,3]-shift to spiro-fused 2,5-cyclohexadienones

Spiro-fused 2,5-cyclohexadienones from the thermal 1,3-alkyl migrations of quinol vinyl ethers. A strategy for conversion of a carbonyl carbon to a quaternary carbon