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One‐Pot Synthesis of Aryl‐ and Alkyl S ‐Perfluoroalkylated NH ‐Sulfoximines from Sulfides
Author(s) -
Chaabouni Slim,
Lohier JeanFrançois,
Barthelemy AnneLaure,
Glachet Thomas,
Anselmi Elsa,
Dagousset Guillaume,
Diter Patrick,
Pégot Bruce,
Magnier Emmanuel,
Reboul Vincent
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805055
Subject(s) - aryl , chemistry , alkyl , medicinal chemistry , ammonium , carbamate , organic chemistry , stereochemistry
A general efficient one‐pot synthesis of S ‐perfluoroalkylated NH ‐sulfoximines from sulfides has been developed using phenyliodine diacetate (PIDA) and ammonium carbamate. Remarkable rate enhancement with trifluoroethanol was observed, presumably due to H‐bonding effects. These mild and metal‐free conditions are compatible with ‐CH 2 F, ‐CFCl 2 , ‐CF 2 H, ‐CF 2 Br, ‐C 4 F 9 , and ‐CF 3 groups, in both the alkyl‐ and aryl series. Based on a 19 F NMR analysis, a λ 6 ‐acetoxysulfanenitrile intermediate was proposed.