Transition from Kwon [4+2]- to [3+2]-cycloaddition enabled by AgF-assisted phosphine catalysis.

ABSTRACT: Phosphine catalysis generally relies on the potential of carbanion-phosphonium zwitterions that are generated via nucleophilic addition of phosphine catalyst to electrophilic reactants. Consequently, structural modification of zwitterions using distinct electrophilic reactants has emerged as a prominent strategy to enhance catalysis diversity. Herein, we present an alternative strategy that utilizes AgF additive to expand phosphine catalysis. We find that AgF can readily transform the canonical carbanion-phosphonium zwitterion into silver enolate-fluorophosphorane intermediate, eventually furnishing a P(III)/P(V) catalytic cycle. This strategy has been successfully applied to the phosphine-catalyzed reaction of 2-substituted allenoate and imine, resulting in the transition from Kwon [4 + 2

SUBMITTER: Qian J 

PROVIDER: S-EPMC11324788 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature