Nickel-catalyzed Markovnikov 1,2-Hydroboration of In Situ Generated 1,3-Dienes Using a Secondary Homoallylic Carbonate as the 1,3-Diene and Hydride Source

Abstract

Transition metal-catalyzed regioselective hydroboration of 1,3-dienes has received continuous interest in the field of organic synthesis. Herein, we describe the nickel-catalyzed Markovnikov 1,2-hydroboration of in situ generated 1,3-dienes with bis(pinacolato)diboron using a secondary homoallyic carbonate as the 1,3-diene and hydride source. The catalytic hydroboration of in situ generated 1,3-dienes proceeded in the presence of Ni(cod)2/P(p-MeOC6H4)3 as the catalyst to give the corresponding secondary allylic boronates in 42–77% yields with high regioselectivity (12 examples).