Radical trans-Hydroboration of Alkynes with N-Heterocyclic Carbene Boranes

Angewandte Chemie
Masaki ShimoiTsuyoshi Taniguchi

Abstract

Hydroboration of internal alkynes with N-heterocyclic carbene boranes (NHC-boranes) occurs to provide stable NHC (E)-alkenylboranes upon thermolysis in the presence of di-tert-butyl peroxide. The E isomer results from an unusual trans-hydroboration, and the E/Z selectivity is typically high (90:10 or greater). Evidence suggests that this hydroboration occurs by a radical-chain reaction involving addition of an NHC-boryl radical to an alkyne to give a β-NHC-borylalkenyl radical. Ensuing hydrogen abstraction from the starting NHC-borane provides the product and returns the starting NHC-boryl radical. Experiments suggest that the observed trans-selectivity results from kinetic control in the hydrogen-transfer reaction.

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Citations

Apr 6, 2019·Organic & Biomolecular Chemistry·Anne-Laure Vallet, Emmanuel Lacôte
Jun 13, 2019·Chemistry : a European Journal·Lauren E Longobardi, Alois Fürstner
Sep 19, 2019·Chemical Communications : Chem Comm·Yun-Shuai HuangYi-Feng Wang
Nov 2, 2019·Angewandte Chemie·Masaki ShimoiTsuyoshi Taniguchi
Nov 13, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Krishna K ManarSanjay Singh
Feb 6, 2020·Chemical Science·Florian W Friese, Armido Studer
Jan 23, 2021·Organic Letters·Kosuke TakahashiTsuyoshi Taniguchi
Mar 30, 2021·Angewandte Chemie·Mingbing ZhongThomas Poisson
May 19, 2021·Chemical Society Reviews·Megan Amy Bryden, Eli Zysman-Colman
May 5, 2021·Chemistry : a European Journal·Maude AeltermanThomas Poisson
May 26, 2021·Organic Letters·Karen de la Vega-HernándezAlejandro Perez-Luna
Jul 13, 2021·Chemical Society Reviews·Tsuyoshi Taniguchi
Sep 17, 2019·Journal of the American Chemical Society·Kensuke YamamotoShinichi Saito
Jul 16, 2020·Journal of the American Chemical Society·Qiang FengJianwei Sun
Nov 30, 2018·Journal of the American Chemical Society·Karen de la Vega-HernándezAlejandro Perez-Luna
Jan 5, 2022·Chemistry : a European Journal·Tsuyoshi Taniguchi

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