Visible-Light-Promoted C(sp3)-C(sp3) Cross-Coupling of Amino Acids and Aryl Trifluoromethyl Ketones Through Simultaneous Decarboxylation and Defluorination

Org Lett. 2023 Dec 8;25(48):8733-8738. doi: 10.1021/acs.orglett.3c03675. Epub 2023 Nov 22.

Abstract

A photoredox-catalyzed approach for the difluoroalkylation of amino acids was achieved through simultaneous decarboxylation and defluorination processes. This innovative protocol employs commonly available amino acids and trifluoroacetophenones as the primary starting materials, eliminating the necessity for preactivation. This strategy has enabled the synthesis of several difluoroketone functionalized amines in moderate to impressive yields. These synthesized compounds are presented as foundational molecules for subsequent modification. The underlying mechanism for the transformation is anchored in a single electron transfer (SET) radical pathway.