NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors of N-Carbamoylimines

A general and practical N‐iodosuccinimide (NIS)‐promoted aza‐Friedel–Crafts reaction of various aromatic nucleophiles with N‐acylimines generated in situ from α‐amidosulfides to give a rapid access to highly functionalized amines is described. The newly developed methodology is very mild, fast, effi...

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Bibliographic Details
Published in:Chemistry : a European journal 2014-03, Vol.20 (13), p.3621-3625
Main Authors: George, Nicolas, Bekkaye, Mathieu, Alix, Aurélien, Zhu, Jieping, Masson, Géraldine
Format: Article
Language:English
Subjects:
Chemical Sciences
Friedel-Crafts reaction
imines
multicomponent reactions
N-iodosuccinimide
Organic chemistry
tandem reactions
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Summary:A general and practical N‐iodosuccinimide (NIS)‐promoted aza‐Friedel–Crafts reaction of various aromatic nucleophiles with N‐acylimines generated in situ from α‐amidosulfides to give a rapid access to highly functionalized amines is described. The newly developed methodology is very mild, fast, efficient, and complementary. Catalytic activation of­ N,S‐acetals: A general and practical N‐iodosuccinimide (NIS)‐promoted aza‐Friedel–Crafts reaction of various aromatic nucleophiles with N‐acylimines generated in situ from α‐amido‐sulfides is described. The newly developed methodology is very mild, fast, efficient, and complementary (see scheme).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201400117