Radical <i>trans</i>-Hydroboration of Substituted 1,3-Diynes with an <i>N</i>-Heterocyclic Carbene Borane
Kosuke Takahashi, Steven J. Geib, Katsuhiro Maeda, Dennis P. Curran, Tsuyoshi Taniguchi
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.
Topics & Concepts
ChemistryCarbeneHydroborationBoraneCatalysisStereoselectivityMedicinal chemistryOrganic chemistryOrganoboron and organosilicon chemistryRadical Photochemical ReactionsCatalytic Cross-Coupling Reactions