Issue 10, 2020

Pd/light-induced alkyl–alkenyl coupling reaction between unactivated alkyl iodides and alkenylboronic acids

Abstract

Alkyl–alkenyl coupling reaction between unactivated alkyl iodides and 2-arylalkenylboronic acids utilizing a Pd/light combined system was studied. This reaction provided 2-alkylarylalkenes in good yields. It is proposed that in this reaction alkyl radicals are formed by SET from a Pd catalyst to alkyl iodides, which then undergo addition reactions to form C–C double bonds of alkenyl boronic acids and the subsequent β-fragmentation of boronyl radicals leads to the formation of alkyl-substituted arylalkenes.

Graphical abstract: Pd/light-induced alkyl–alkenyl coupling reaction between unactivated alkyl iodides and alkenylboronic acids

Supplementary files

Article information

Article type
Research Article
Submitted
12 Mar 2020
Accepted
13 Apr 2020
First published
16 Apr 2020

Org. Chem. Front., 2020,7, 1266-1270

Pd/light-induced alkyl–alkenyl coupling reaction between unactivated alkyl iodides and alkenylboronic acids

H. Huang, Y. Wang, Y. Wu and I. Ryu, Org. Chem. Front., 2020, 7, 1266 DOI: 10.1039/D0QO00318B

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