Regio- and stereoselective hydrophosphination reactions of alkynes with phosphine-boranes: access to stereodefined vinylphosphine derivatives.

Abstract

Vinylphosphine-borane complexes are easily synthesized by regio- and stereoselective hydrophosphination of terminal alkynes with use of secondary phosphine-boranes as hydrophosphinating agent. The regioselectivity of the reaction is efficiently controlled by the choice of the activation process: thermal or metal catalyst activation. The vinylphosphine derivatives are purified by chromatography on silica gel. Scalability of the process is demonstrated on a gram scale. This simple route should promote the use of vinylphosphines as building blocks for organic and organometallic chemistry.