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One Pot Sequential Synthesis of N ‐[2‐(Phenylsulfinyl)phenyl]acetamides: A Ring Opening Rearrangement Functionalization (RORF)
Author(s) -
Behera Ahalya,
Rakshit Amitava,
Sahoo Ashish K.,
Patel Bhisma K.
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201801597
Subject(s) - chemistry , surface modification , ring (chemistry) , acetamide , acylation , sulfur , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
A Cu II 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).