Radical trans-Hydroboration of Substituted 1,3-Diynes with an N-Heterocyclic Carbene Borane

Kosuke Takahashi; Steven J Geib; Katsuhiro Maeda; Dennis P Curran; Tsuyoshi Taniguchi

doi:10.1021/acs.orglett.0c04284

Radical trans-Hydroboration of Substituted 1,3-Diynes with an N-Heterocyclic Carbene Borane

Org Lett. 2021 Feb 5;23(3):1071-1075. doi: 10.1021/acs.orglett.0c04284. Epub 2021 Jan 22.

Authors

Kosuke Takahashi, Steven J Geib¹, Katsuhiro Maeda, Dennis P Curran¹, Tsuyoshi Taniguchi

Affiliation

¹ Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, United States.

PMID: 33481616
DOI: 10.1021/acs.orglett.0c04284

Abstract

Monohydroboration of substituted 1,3-diynes with an N-heterocyclic carbene borane (NHC-borane) occurs under radical conditions using an azo initiator, such as ACCN and AIBN, and a thiol as a polarity-reversal catalyst. The reaction is highly regio- and stereoselective and provides stable NHC-(E)-alkynylalkenylboranes.