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

Zuli Wang; Lei Wang; Pinhua Li

doi:10.1055/s-2008-1072562

PAPER

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

Zuli Wang^a, Lei Wang*^a,b, Pinhua Li^a
^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;

Abstract

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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.

Key words

Sonogashira coupling reaction - organic-inorganic hybrid material - silica-anchored proline-copper(I) catalyst - heterogeneous catalysis - terminal alkynes - aryl iodides - aryl bromides

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