Nickel-Catalyzed Homo- and Cross-Coupling of Allyl Alcohols via Allyl Boronates
Yi Gan, Hui Hu, Yuanhong Liu
Abstract
A nickel-catalyzed homo- and cross-coupling of allylic alcohols to 1,5-dienes in the presence of B2pin2 with excellent regioselectivity has been developed. Mechanistic studies indicate that the reaction proceeds via sequential nickel-catalyzed borylation of allyl alcohols followed by cross-coupling of the resulting allyl boronates with allyl alcohols. The method was effectively applied to nickel-catalyzed allylation of aldehydes using allylic alcohols directly.
Topics & Concepts
ChemistryAllylic rearrangementCatalysisRegioselectivityNickelAllyl alcoholCoupling (piping)Organic chemistryMedicinal chemistryMechanical engineeringEngineeringOrganoboron and organosilicon chemistryCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis