Stereoselective Synthesis of Functionalized 1,3‐Enynes through Recyclable Copper(I)‐Catalyzed Three‐Component Reaction of Terminal Alkynes, Diazoesters and Aldehydes

Abstract

AbstractA highly efficient heterogeneous copper(I)‐catalyzed three‐component coupling of terminal alkynes, diazoesters and aldehydes has been achieved by using 10 mol% of copper(I) iodide complex [N,N‐CuI‐MCM‐41] anchored on 2‐aminoethylamino‐modified mesoporous material MCM‐41 as the catalyst under mild conditions, delivering a wide variety of 2‐alkoxycarbonyl‐substituted (E)‐1,3‐enynes in mostly good to high yields with excellent stereoselectivity. The heterogenized copper(I) complex can be facilely prepared from inexpensive reagents by using a simple procedure and exhibits a remarkably higher catalytic activity than CuI, and can be recycled more than ten times without a significant drop in its catalytic efficiency. This protocol represents the first example of heterogeneous copper‐catalyzed stereoselective construction of functionalized 1,3‐enynes from simple and commercially available starting materials.