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

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.