Copper-Catalyzed Cascade Cyclization Reactions of Diazo Compounds with tert-Butyl Nitrite and Alkynes: One-Pot Synthesis of Isoxazoles.

Abstract

A novel copper-catalyzed [3 + 2] cycloaddition reaction of alkynes with nitrile oxides generated in situ from the coupling reaction of copper carbene and nitroso radical has been developed. The three-component reaction provides a simple and efficient method for the construction of isoxazoles in a highly regioselective manner in a single step. On the basis of the experimental results and density functional theory calculations, a catalytic cycle (CuI-CuII-Cu0-CuI) for this cascade cyclization reaction is proposed.