Diastereoselective, Catalytic Pd(II)-Based Allylic Alkylation

Significance

The methodology described in this report is one of the first direct catalytic allylic C-H alkylation reactions. White and Young have introduced a novel set of reaction conditions, allowing the reaction to proceed in a truly catalytic fashion. The use of DMSO as an π-acceptor ligand facilitates nucleophilic functionalization of the π-allylPd intermediate, while the combination of sterically bulkier 2,6-dimethylbenzoquinone (DMBQ) and AcOH serves as an oxidant, activating agent of π-allylPd species toward reductive elimination and as a source of catalytic base.