NHC-Copper-Catalyzed Tandem Hydrocupration and Allylation of Alkenyl BoronatesSupported by: National Research Foundation of Korea grant (NRF-2016R1A2B4011719) funded by the Korean government (MEST).
Received: 03 March 2017
Accepted after revision: 04 April 2017
03 May 2017 (eFirst)
Published as part of the Special Topic Modern Strategies for Borylation in Synthesis
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.