Photoredox Radical Truce-Smiles Rearrangement of N- Sulfinyl Acrylamides with Bromodifluoroacetamides

Org Lett. 2024 Dec 18. doi: 10.1021/acs.orglett.4c04484. Online ahead of print.

Abstract

We herein report a photochemical Truce-Smiles rearrangement reaction of N-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon-centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce-Smiles rearrangement methods involving N-sulfonyl acrylamides.