Electro‐Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Open Access
- 23 March 2020
- journal article
- research article
- Published by Wiley in Chemistry – A European Journal
- Vol. 26 (38), 8382-8387
- https://doi.org/10.1002/chem.202001394
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 via 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.Funding Information
- Deutsche Forschungsgemeinschaft (DI 2227/2-1, JA 2794/1-1, SFB 749)
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