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Review | Special issue | Vol 80, No. 2, 2010, pp.697-724
Published online, 12th August, 2009
DOI: 10.3987/REV-09-SR(S)5
Carbonylative Palladium-Catalyzed Reactions of Lactam-, Lactone-, and Thiolactone-Derived Vinyl Triflates and Phosphates for the Synthesis of N-, O-, and S-Heterocycles

Ernesto G. Occhiato,* Dina Scarpi, and Cristina Prandi*

*Dipartimento di Chimica Organica “Ugo Schiff”, Università di Firenze, Via della Lastruccia n. 13, I-50019 Sesto Fiorentino (Fi), Italy

Abstract

A full account of our most recent studies on the chemistry of lactam-, lactone-, and thiolactone-derived vinyl triflates and phosphates is reported. In this review we focus on the use of these versatile electrophiles in Pd-catalyzed carbonylative reactions. They provide, through alkoxycarbonylation, aminocarbonylation and carbonylative Suzuki-Miyaura reactions, a straightforward and convenient access to useful intermediates for the synthesis of N-, O- and S-heterocyclic and natural compounds.