Selective multifunctionalization of N-heterocyclic carbene boranes via the intermediacy of boron-centered radicals.

ABSTRACT

The selective difunctionalization of N-heterocyclic carbene (NHC) boranes with alkenes has been achieved via decatungstate and thiol synergistic catalysis. The catalytic system also allows stepwise trifunctionalization, leading to complex NHC boranes with three different functional groups which are challenging to prepare by other methods. The strong hydrogen-abstracting ability of the excited decatungstate enables the generation of boryl radicals from mono- and di-substituted boranes for realizing borane multifunctionalization. This proof-of-principle research provides a new chance for fabricating unsymmetrical boranes and developing boron-atom-economic synthesis.