Organic Chemistry Portal



Intramolecular PIFA-Mediated Alkyne Amidation and Carboxylation Reaction

Imanol Tellitu,* Sonia Serna, M. Teresa Herrero, Isabel Moreno, Esther Domínguez and Raul SanMartin

*Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología, Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), P.O. Box 644, 48080 Bilbao, Spain, Email:

I. Tellitu, S. Serna, M. T. Herrero, I. Moreno, E. Domínguez, R. SanMartin, J. Org. Chem., 2007, 72, 1526-1529.

DOI: 10.1021/jo062320s


The hypervalent iodine reagent PIFA promotes the efficient intramolecular electrophilic cyclization of easily accessible alkynylamides and alkynyl carboxylic acids, leading to pyrrolidinone and lactone skeletons, respectively. A synthetic study and a mechanistic proposal for these transformations are presented.

see article for more examples

Key Words

PIFA, lactones, lactams

ID: J42-Y2007-0650