A metal-free approach to the synthesis of indoline derivatives by a phenyliodine(III) bis(trifluoroacetate)-mediated amidohydroxylation reaction.
A novel approach to the synthesis of indoline derivatives is presented. The key cyclization step features the phenyliodine(III) bis(trifluoroacetate)- (PIFA-) mediated formation of a N-acylnitrenium ion and its succeeding intramolecular trapping by the olefin fragment. In addition, difunctionalization of the alkene moiety is achieved since the in situ generation of an additional hydroxy group at the terminal position of the original double bond accompanies the intramolecular C-N bond formation.
Correa
Arkaitz
A
Departamento de Química Organica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco - Euskal Herriko Unibertsitatea, P.O. Box 644, 48080 Bilbao, Spain.
Tellitu
Imanol
I
Domínguez
Esther
E
SanMartin
Raul
R