Visible-Light-Promoted Dual Photoredox/Nickel-Catalyzed Chemoselective Reduction of Secondary and Tertiary Amides with Hydrosilanes in the Presence of an Ester

J Org Chem. 2023 Feb 17;88(4):2122-2131. doi: 10.1021/acs.joc.2c02543. Epub 2023 Feb 2.

Abstract

We report a one-step procedure to selectively reduce secondary and tert-amides to their corresponding amine derivatives in the presence of an ester. This was achieved via the synergistic combination of a photoredox, a nickel catalytic system, and phenyl silane as a reductant in the presence of blue light-emitting diode light (455 nm) at room temperature. Further, this mild light-promoted dual metallaphotoredox catalytic system was also successful in selectively reducing a lactam to the cyclic amines, without affecting the ester moiety present in the molecules.