Cobalt-Catalyzed Multicomponent Carbonylation of Olefins: Efficient Synthesis of β-Perfluoroalkyl Imides, Amides, and Esters

Abstract

A general and broadly applicable cobalt-catalyzed multicomponent 1,2-perfluoroalkylation carbonylation of alkenes has been developed. This protocol allows the synthesis of β-perfluoroalkyl-substituted amides, esters, and related derivatives using olefins, carbon monoxide, commercially accessible perfluoroalkyl iodides, and a variety of nucleophiles including low nucleophilic amides and urea derivatives in a one-pot manner. As an example, readily available trifluoroiodomethane can be utilized forming pharmaceutically relevant β-trifluoromethylated amides. To showcase the application potential, the perfluoroalkylation carbonylation process was applied to selected current drugs and biologically active molecules. The methodology permits a straightforward increase of the molecular complexity of olefins toward functionalized perfluoroalkylated building blocks in a regioselective manner.