Phosphine-catalyzed remote ß-C-H functionalization of amines triggered by trifluoromethylation of alkenes: one-pot synthesis of bistrifluoromethylated enamides and oxazoles.
Angew Chem Int Ed Engl
; 54(13): 4041-5, 2015 Mar 23.
Article
em En
| MEDLINE
| ID: mdl-25694337
ABSTRACT
An unprecedented phosphine-catalyzed remote ß-CH 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 ß-C sp 3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.
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Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oxazóis
/
Fosfinas
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Polímeros de Fluorcarboneto
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Alcenos
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Amidas
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Aminas
Idioma:
En
Revista:
Angew Chem Int Ed Engl
Ano de publicação:
2015
Tipo de documento:
Article