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Copper‐Catalyzed Perfluoroalkylthiolation of Alkynes with Perfluoroalkanesulfenamides
Author(s) -
Tlili Anis,
Alazet Sébastien,
Glenadel Quentin,
Billard Thierry
Publication year - 2016
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.201601338
Subject(s) - copper , reagent , catalysis , reactivity (psychology) , ligand (biochemistry) , base (topology) , combinatorial chemistry , chemistry , organic chemistry , mathematics , medicine , mathematical analysis , biochemistry , alternative medicine , receptor , pathology
Copper‐catalyzed direct perfluoroalkylthiolation of alkynes by using the corresponding perfluoroalkanesulfenamide reagent is reported. The selective mono‐ and bis‐perfluoroalkylthiolation of alkynes can be conducted under very mild conditions (no base, room temperature) in very good to excellent yields. This approach, which uses a low toxicity, inexpensive copper catalyst that incorporates a commercially available ligand, is applied in the absence of any additional base. Preliminary mechanistic investigations shed some light on the nature of the unprecedented reactivity observed.