Premium
Fe(OTf) 2 ‐Catalyzed Thia ‐Michael Addition Reaction: A Green Synthetic Approach to β‐Thioethers
Author(s) -
Lauzon Samuel,
Li Mao,
Keipour Hoda,
Ollevier Thierry
Publication year - 2018
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.201800780
Subject(s) - michael reaction , chemistry , catalysis , derivatization , addition reaction , green chemistry , organic chemistry , reaction conditions , reaction mechanism , combinatorial chemistry , high performance liquid chromatography
A convenient Fe(OTf) 2 ‐catalyzed Michael addition reaction of thiols to α,β‐unsaturated carbonyl compounds was developed. The use of a simple procedure (EtOH, room temperature, air atmosphere) allowed to set up effective green catalytic conditions for C–S bond formation. The scope of the reaction was demonstrated using various substituted thiols and original Michael acceptors. The corresponding β‐thioethers were obtained in good to excellent yields (up to 99 %). Also, the derivatization into the one‐pot thia ‐Michael addition/oxidation reaction of 3‐[3‐(phenylthio)butanoyl]oxazolidin‐2‐one using H 2 O 2 has proven to be efficient.