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

被引：22

作者：

Baumann, Andreas N. ^{[1
]}

Music, Arif ^{[1
]}

Dechent, Jonas ^{[1
]}

Mueller, Nicolas ^{[1
]}

Jagau, Thomas C. ^{[1
]}

Didier, Dorian ^{[1
]}

机构：

[1] Ludwig Maximilians Univ Munchen, Dept Chem & Pharm, Butenandtstr 5-13,Haus F, D-81377 Munich, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2020年 / 26卷 / 38期

关键词：

catalyst-free; electrochemistry; olefination; organoborates; stereoconvergent; STEREOSELECTIVE-SYNTHESIS; ORGANIC HALIDES; REAGENTS; ALKYNES; ENYNES; ARYL;

D O I：

10.1002/chem.202001394

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：8382 / 8387

页数：6

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