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CuI‐Mediated α‐Ketoacylation of Sulfoximines under Solvent‐Free Conditions
Author(s) -
Zou Ya,
Peng Zhihong,
Dong Wanrong,
An Delie
Publication year - 2015
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.201500410
Subject(s) - chemistry , aryl , solvent , catalysis , catalytic cycle , combinatorial chemistry , compatibility (geochemistry) , organic chemistry , chemical engineering , alkyl , engineering
The first preparation of α‐ketoacyl sulfoximines under solvent‐free conditions using aryl ethanones and NH ‐sulfoximines has been discovered and a series of desired 2‐oxo‐2‐arylacetyl sulfoximines were successfully synthesized in good to excellent yields (up to 93 %). The unprecedented protocol requires no extra solvents, bases, or additives and demonstrates outstanding compatibility with assorted functional groups (up to 27 examples). A plausible double catalytic cycle mechanism involving elemental iodine and copper is proposed; in‐situ generated aryl‐α‐iodo‐ethanone and a sulfoximine‐liganded‐Cu II intermediate play important roles in C(sp 3 )–N coupling. The postulated mechanism is inspired by key experimental investigations detailed here.