Base-Mediated a-gem-Difluoroalkenylations of Aldehydes and Ketones

Herein, we present a base-mediated nucleophilic substitution reaction of a-trifluoromethylstyrenes with simple silyl enol ethers, enabling the efficient synthesis of carbonyl-substituted gem-difluoroalkenes. The merit of this protocol is exhibited by its mild reaction conditions, broad substrate scope, and scalable preparation. Notably, this method demonstrates its applicability for late-stage functionalization of structurally complex molecules. Moreover, we illustrate that the resulting products can serve as valuable precursors for the synthesis of diverse medicinally relevant compounds.

Automated summary

Here, we describe a base-mediated nucleophilic substitution reaction that efficiently synthesizes carbonyl-substituted gem-difluoroalkenes using simple silyl enol ethers. This protocol offers mild reaction conditions, a broad substrate scope, and scalability. Importantly, it demonstrates the applicability for late-stage functionalization of structurally complex molecules and provides valuable precursors for the synthesis of diverse medicinally relevant compounds.