NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl Boronates

Published as part of the Special Topic Modern Strategies for Borylation in Synthesis

Abstract

A tandem hydrocupration/allylation of alkenyl boronates efficiently proceeds with NHC-copper catalysts using hydrosilane and allyl phosphate as reagents. In the presence of IMes–Cu catalyst, the allylation of in situ generated Β-α-copper intermediates smoothly occurs to give homoallylic boronates in high yields, despite competitive side reaction pathways. Mono- and disubstituted alkenyl boronates were effective in the reaction with terminal allyl phosphates, but trisubstituted substrates showed limited reactivity.

Key words

allylic substitution - copper - homoallylic boronates - hydrocupration - N-heterocyclic carbenes - tandem reaction

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