Dual Triplet Ketone/Nickel Catalysis for the Cross-Coupling of Aryl/Alkyl Bromides with Alkyl Boronic Acids/Boronates through Radical Transfer Strategy.

Abstract

In the present work, we have developed a dual triplet ketone/nickel-catalyzed strategy for C(sp3)-C(sp2) and C(sp3)-C(sp3) cross-coupling between aryl/alkyl bromides and alkyl boronic acids/boronates via an aminyl radical transfer (ART) strategy. The protocol features several attractive advantages, including mild reaction conditions, the use of commercially available and inexpensive starting materials, broad substrate scope, and excellent functional-group tolerance and applicability toward late-stage functionalization. Mechanistic investigations support the dual role of morpholine as both a base and an aminyl radical transfer agent, providing insight into the reaction pathway.