Electro‐Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes

Baumann, Andreas N.; Music, Arif; Dechent, Jonas; Müller, Nicolas; Jagau, Thomas C. und Didier, Dorian (2020): Electro‐Olefination—A Catalyst Free Stereoconvergent Strategy for the Functionalization of Alkenes. In: Chemistry—A European Journal, Bd. 26, Nr. 38: S. 8382-8387

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.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• ISSN: 1521-3765
• Sprache: Englisch