Electro-Olefination-A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes
Open Access
- 8 July 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(sp(2))-C(sp(2)) 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.Keywords
Funding Information
- Deutsche Forschungsgemeinschaft (DI 2227/2-1, JA 2794/1-1, SFB 749)
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