One Pot Sequential Synthesis of N‐[2‐(Phenylsulfinyl)phenyl]acetamides: A Ring Opening Rearrangement Functionalization (RORF)

Abstract

A CuII catalyzed one‐pot sequential synthesis of N‐[2‐(phenylthio)phenyl]acetamides from benzo[d]thiazol‐2‐amines, iodoarenes and carboxylic acids (RCOOH) has been accomplished via ring opening rearrangement functionalization (RORF). Here, the ring opening is associated with the loss of carbon and nitrogen atoms with concurrent S‐arylation and N‐acylation leading to ortho‐bifunctionalized products. A further sequential addition of tert‐butyl hydroperoxide (TBHP) results in the formation of a sulfur oxidized product, N‐[2‐(phenylsulfinyl)phenyl]acetamide. A plausible mechanism has been proposed for this unprecedented ring opening rearrangement functionalization (RORF).