Unlocking Amides through Selective C-N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups

Org Lett. 2021 Dec 17;23(24):9419-9424. doi: 10.1021/acs.orglett.1c03541. Epub 2021 Nov 16.

Abstract

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, N-acyl compounds (esters, thioesters, amides), and N-sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

Publication types

  • Research Support, Non-U.S. Gov't