Synthesis 2008(9): 1367-1372  
DOI: 10.1055/s-2008-1072562
PAPER
© Georg Thieme Verlag Stuttgart · New York

Silica-Anchored Proline-Copper(I) as an Efficient and Recyclable Catalyst for the Sonogashira Reaction

Zuli Wanga, Lei Wang*a,b, Pinhua Lia
a Department of Chemistry, Huaibei Coal Teachers College, Huaibei, Anhui 235000, P. R. of China
Fax: +86(561)3090518; e-Mail: leiwang@hbcnc.edu.cn;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
Fax: +86(561)3802069;
Further Information

Publication History

Received 10 December 2007
Publication Date:
27 March 2008 (online)

Abstract

A novel silica-anchored proline-copper(I) organic-inorganic hybrid material as an efficient catalyst for the Sonoga­shira reaction was developed. Terminal alkynes were reacted with aryl iodides and bromides smoothly in the presence of a proline-functionalized silica-anchored copper(I) catalyst in DMF to afford the corresponding cross-coupling products in good to excellent yields. Furthermore, silica-anchored proline-copper(I) catalyst was recovered and recycled by a simple filtration of the reaction solution and reused for six times without significant decreases in activity.