Superacid‐Catalyzed Trifluoromethylthiolation of Aromatic Amines

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...

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Bibliographic Details
Published in:Angewandte Chemie 2017-01, Vol.129 (1), p.175-178
Main Authors: Bonazaba Milandou, Longin Justin Clair, Carreyre, Hélène, Alazet, Sébastien, Greco, Gino, Martin‐Mingot, Agnès, Nkounkou Loumpangou, Célestine, Ouamba, Jean‐Maurille, Bouazza, Fodil, Billard, Thierry, Thibaudeau, Sébastien
Format: Article
Language:English
Subjects:
Activation
Alkaloids
Amines
Chemical Sciences
Chemistry
Intermediates
Magnetic resonance spectroscopy
NMR
NMR spectroscopy
Nuclear magnetic resonance
Organic chemistry
Reagents
Steroid hormones
Steroids
Substrates
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Summary: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.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201609574