Study of Different Copper (I) Catalysts for the “Click Chemistry” Approach to Carbanucleosides

Abstract

We compare herein the scope of three copper (I) catalysts on the synthesis of various 1,4-disubstitued-1,2,3-triazolo-carbanucleosides through a microwave (and thermic) assisted Huisgen 1,3-dipolar cycloaddition. The tetrakis(acetonitrile)copper hexafluorophosphate ([Cu(CH ₃ CN)₄]PF ₆ ), the imidazoline(mesythyl)copper bromide (Imes)CuBr, and the copper/copper sulfate Cu(0)/CuSO ₄ (II) mixture have been chosen for this study. Their influence in a catalytic amount will be analyzed according to the substituent of the alkyne, the solvent, or the heating method.

Keywords:

• Carbanucleosides
• Huisgen
• 1,3-dipolar cycloaddition

Acknowledgments

These studies were supported in part by a grant from Aventis Pharma (Sanofi-Aventis group) and Bayer Pharma as part of a multi-organism call for proposals, and in part by an “ANR-05-BLAN-0368-03.”