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Updated: Dec 25, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Electro-Olefination-A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Andreas N Baumann1, Arif Music1, Jonas Dechent1
1Department of Chemistry and Pharmacy, Ludwig-Maximilians-University Munich, Butenandtstraße 5-13, Haus F, 81377, Munich, Germany.
Abstract:
Conventional methods carrying out C(sp2 )-C(sp2 ) bond formations are typically mediated by transition-metal-based catalysts. Herein, we conceptualize a complementary avenue to access such bonds by exploiting the potential of electrochemistry in combination with organoboron chemistry. We demonstrate a transition metal catalyst-free electrocoupling between (hetero)aryls and alkenes through readily available alkenyl-tri(hetero)aryl borate salts (ATBs) in a stereoconvergent fashion. This unprecedented transformation was investigated theoretically and experimentally and led to a library of functionalized alkenes. The concept was then carried further and applied to the synthesis of the natural product pinosylvin and the derivatization of the steroidal dehydroepiandrosterone (DHEA) scaffold.
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