Copper-Catalyzed Preparation of gamma-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions

Samuel Inack-Ngi (1) , Raphaël Rahmani (2) , Laurent Commeiras (2) , Gaëlle Chouraqui (2) , Jérôme Thibonnet (1) , Alain Duchêne (1) , Mohamed Abarbri (1) , Jean-Luc Parrain (2)

1 PCMB - EA4244 - Laboratoire Physicochimie des matériaux et des biomolécules
2 STeRéO

A general and efficient copper(I)-catalyzed cross-coupling and heterocyclization reaction of terminal alkynes and b-iodo-a,b-unsaturated acid dérivatives has been developed under very mild conditions. This method provides easy access from good to excellent yields of a variety of 5-ylidenebutenolides and 3-substituted isocoumarins with excellent regioand stereoselectivity. This procedure does not require the use of any expensive supplementary additives, and is palladium-free.

Mots clés: Alkynes; Copper; Cross-coupling; Homogeneous catalysis; lactones

Domaines: Chimie organique

Samuel Inack-Ngi, Raphaël Rahmani, Laurent Commeiras, Gaëlle Chouraqui, Jérôme Thibonnet, et al.. Copper-Catalyzed Preparation of gamma-Alkylidenebutenolides and Isocoumarins under Mild Palladium-Free Conditions. Advanced Synthesis and Catalysis, 2009, 351, pp.779 - 788. ⟨10.1002/adsc.200800757⟩. ⟨hal-00678956⟩