Premium
Superacid‐Catalyzed Trifluoromethylthiolation of Aromatic Amines
Author(s) -
Bonazaba Milandou Longin Justin Clair,
Carreyre Hélène,
Alazet Sébastien,
Greco Gino,
MartinMingot Agnès,
Nkounkou Loumpangou Célestine,
Ouamba JeanMaurille,
Bouazza Fodil,
Billard Thierry,
Thibaudeau Sébastien
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609574
Subject(s) - superacid , chemistry , catalysis , reagent , substrate (aquarium) , surface modification , molecule , combinatorial chemistry , organic chemistry , organic molecules , trifluoromethylation , nuclear magnetic resonance spectroscopy , trifluoromethyl , oceanography , alkyl , geology
Upon activation under superacid conditions, functionalized tailor‐made N‐SCF 3 sulfenamides served as reagents for the trifluoromethylthiolation of aromatic amines. This method has a broad substrate scope and can be used for the late‐stage functionalization of complex molecules such as alkaloids or steroids. Mechanistic studies based on in situ low‐temperature NMR spectroscopy revealed the involvement of dicationic superelectrophilic intermediates.