Issue 38, 2021

Copper-catalyzed regioselective trans-silaboration of internal arylalkynes with stereochemical switch to cis-addition mode

Abstract

Copper-catalyzed silafunctionalization of alkynes using a silylboronic ester as a silicon source has recently progressed rapidly. Generally, the reaction affords a product with cis-stereoselectivity. We herein describe trans-selective 1,2-addition of silylboronic esters to internal arylalkynes, which was promoted efficiently by the CuOt-Bu/RCy2P/NaOt-Bu catalysts. Moreover, we report a stereochemical switch to cis-addition in the reactions of Me2(i-PrO)Si–B(pin) in hydrocarbon solvents including cyclohexane.

Graphical abstract: Copper-catalyzed regioselective trans-silaboration of internal arylalkynes with stereochemical switch to cis-addition mode

Supplementary files

Article information

Article type
Communication
Submitted
24 Mar 2021
Accepted
04 Apr 2021
First published
05 Apr 2021

Chem. Commun., 2021,57, 4670-4673

Copper-catalyzed regioselective trans-silaboration of internal arylalkynes with stereochemical switch to cis-addition mode

T. Ohmura, Y. Takaoka and M. Suginome, Chem. Commun., 2021, 57, 4670 DOI: 10.1039/D1CC01579F

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