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.

Cyclizations of N-acyliminium ions.

Synthetic methods for azaheterocyclic phosphonates and their biological activity.

An Efficient Asymmetric Epoxidation Method for trans-Olefins Mediated by a Fructose-Derived Ketone

Chiral heterocycles by iminium ion cyclization.

Synthesis of optically active piperidine and pyrrolidine alkaloids from L-lysine, L-ornithine, or L-proline using anodic oxidation as key steps

Syntheses des (±)-elaekanine A et C, (±)-trachelanthamidine et (±)-isoretronecanol a partir de methoxy-2 pyrrolidinecarboxylates-1 de methyle (pour les elaekanines) et de benzyle (pour les 2 autres composes)

Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared α-methoxy carbamates as key intermediates

A new [3 + 3]-type annelation useful for the formation of piperidine skeletons

Methoxylation electrochimique de pyrrolidide et morpholide de l'acide p-toluenesulfonique et de N,N-dialkyl-phosphoramidate de diethyle. Application a la synthese du tryptophane a partir de tosyl-1 methoxy-2 prolinate de methyle

Electroorganic chemistry. 81. Anodic oxidation of sulfonamides and amidophosphates

Electroorganic chemistry. 79. Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared .alpha.-methyoxy carbamates as key intermediates

Kenshi Uchida

Papers

Synthesis of optically active piperidine and pyrrolidine alkaloids from L-lysine, L-ornithine, or L-proline using anodic oxidation as key steps

Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared α-methoxy carbamates as key intermediates

A new [3 + 3]-type annelation useful for the formation of piperidine skeletons

Electroorganic chemistry. 81. Anodic oxidation of sulfonamides and amidophosphates

Electroorganic chemistry. 79. Efficient synthesis of pyrrolizidine and indolizidine alkaloids utilizing anodically prepared .alpha.-methyoxy carbamates as key intermediates