Practical procedure for copper(I)-catalyzed allylic boryl substitution with stoichiometric alkoxide base

Abstract

We have developed a useful procedure for borylation using catalytic CuCl/Xantphos and stoichiometric K(O-t-Bu): the highly versatile method is suitable for the synthesis of allylboronates including those with terminal and internal allylic systems, cyclic structures, and functional groups. Optically active allylboronates were synthesized from prochiral substrates with a chiral diphosphine ligand using this procedure. The reaction rate is generally higher than the original Cu(O-t-Bu)/ligand catalyst system, which we previously reported.