Unsaturated Carboxylates as Electrophilic Synthons for Transition-Metal-Catalyst-Free Electroreductive Deoxygenative Coupling.

Authors

Jianyou Zhao, Jiaoyang Liu, Zi-Ao Zhang, Zhihui Sun, Fan Wang, Shuai Liu, Zhong-Quan Liu

Published in

Angewandte Chemie (International ed. in English). Pages e6256116. Oct 04, 2026. Epub Oct 04, 2026.

Abstract

The use of ester-derived electrophiles in transition-metal-free electroreductive C(sp³)─C(sp³) bond formation remains largely unexplored. Herein, we report a sacrificial-anode-enabled electroreductive cross-coupling of simple unsaturated carboxylates with unactivated alkyl halides. Aryl, alkenyl, and alkynyl carboxylates are readily incorporated, affording methylene-bridged alkylarenes together with allylic and propargylic C(sp³)-rich frameworks under mild conditions. Mechanistic studies support independent single-electron reduction of both electrophilic partners, followed by radical-radical coupling, alkoxide elimination, and cathodic deoxygenation via a Clemmensen-like reduction pathway. This work establishes unsaturated carboxylates as a new class of alkylating reagents for electroreductive C(sp³)─C(sp³) bond formation.

PMID:
42829830
Bibliographic data and abstract were imported from PubMed on 04 Oct 2026.

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