Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance

Abstract

Electrochemistry represents one of the most intimate ways of interacting with molecules. This review discusses advances in synthetic organic electrochemistry since 2000. Enabling methods and synthetic applications are analyzed alongside innate advantages as well as future challenges of electroorganic chemistry.

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

“…These results led us to conrm the presence of radical intermediates during electrolysis. In fact, literature reports 16,17,22,25 have already demonstrated a mechanism via electrophilic aromatic substitution for the similar transformation. A putative reaction mechanism was proposed as illustrated in Scheme 5b.…”

“…Adopting electron as "reagent" in place of stoichiometric amounts of oxidants or reductants, electrosynthesis has been recognized as an eco-friendly synthetic tool. 22,23 As part of our continuous works on electrochemical (pseudo)halogenation reactions, 24 herein we present an efficient, low-cost, catalyst-and oxidantfree approach for thio-and selenocyanation of electron-rich arenes using thio-or selenocyanate salts as the sole reagent under mild electrochemical condition (Scheme 1f).…”

Selective C(sp3)−H Aerobic Oxidation Enabled by Decatungstate Photocatalysis in Flow

“…Following this strategy, hydrogen atoms can be abstracted to produce highly reactive radical species, which are subsequently trapped in a wide variety of synthetically useful transformations. This synthetic pathway can be considered appealing, since the transformation is promoted by the use of photons or electrons as traceless reagents, thus simplifying the catalytic systems involved and reducing the environmental impact of the transformation itself 12, 13b…”

Elektrifizierung der organischen Synthese

“…[10] Recently,B aran and co-workers published ag eneral overview on electroorganic developments since 2000. [11] It was our aim to write aReview with aclear focus on synthetic developments that are of great importance in contemporary synthesis: -e lectrochemical fluorination -e lectrochemical C À Nfunctionalization of arenes -K olbe electrolysis Angewandte Chemie Reviews 5596 www.angewandte.org -e lectrochemical arene couplings -e lectrochemical construction of heterocycles -e lectrochemistry in the synthesis of natural products, related compounds,and late-stage functionalization…”