In:
Angewandte Chemie, Wiley, Vol. 127, No. 13 ( 2015-03-23), p. 4113-4117
Abstract:
An unprecedented phosphine‐catalyzed remote β‐CH functionalization of amine derivatives triggered by trifluoromethylation of an alkene with Togni’s reagent was disclosed. This reaction proceeded through the highly selective and concomitant activation of an unactivated alkene and the β‐C H bond of an amine derivative, providing bistrifluoromethylated enamides in excellent yields with good regio‐, chemo‐, and stereoselectivity. Furthermore, the newly developed one‐pot protocol provides a facile and step‐economical access to valuable trisubstituted 5‐(trifluoromethyl)oxazoles. Mechanistic studies showed that this reaction may initiate with a novel phosphine‐catalyzed radical trifluoromethylation of unactivated alkene via a phosphorus radical cation.
Type of Medium:
Online Resource
ISSN:
0044-8249
,
1521-3757
DOI:
10.1002/ange.v127.13
DOI:
10.1002/ange.201412310
Language:
German
Publisher:
Wiley
Publication Date:
2015
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505872-7
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1479266-7
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