Amine Catalysis for the Organocatalytic Diboration of Challenging Alkenes

Chemistry. 2016 Dec 5;22(49):17552-17556. doi: 10.1002/chem.201603979. Epub 2016 Oct 26.

Abstract

The generation of in situ sp2 -sp3 diboron adducts has revolutionised the synthesis of organoboranes. Organocatalytic diboration reactions have represented a milestone in terms of unpredictable reactivity of these adducts. However, current methodologies have limitations in terms of substrate scope, selectivity and functional group tolerance. Here a new methodology based on the use of simple amines as catalyst is reported. This methodology provides a completely selective transformation overcoming current substrate scope and functional/protecting group limitations. Mechanistic studies have been included in this report.

Keywords: Lewis base; amines; density functional calculations; organoboron; organocatalysis.