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• Dai, C
• Cheng, Y
• Cui, J
• Wang, B
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• Dai, C
• Cheng, Y
• Cui, J
• Wang, B
• [+] on PubMed
• Dai, C
• Cheng, Y
• Cui, J
• Wang, B

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Molecules 2010, 15(8), 5768-5781; doi:10.3390/molecules15085768

Review

Click Reactions and Boronic Acids: Applications, Issues, and Potential Solutions

Chaofeng Dai, Yunfeng Cheng, Jianmei Cui and Binghe Wang*

Department of Chemistry and Center for Biotechnology and Drug Design, Georgia State University, Atlanta, Georgia, 30303, USA

* Author to whom correspondence should be addressed.

Received: 30 June 2010; in revised form: 27 July 2010 / Accepted: 4 August 2010 / Published: 23 August 2010

(This article belongs to the Special Issue Click Chemistry)

Download PDF Full-Text [156 KB, uploaded 23 August 2010 10:16 CEST]

Abstract: Boronic acids have been widely used in a wide range of organic reactions, in the preparation of sensors for carbohydrates, and as potential pharmaceutical agents. With the growing importance of click reactions, inevitably they are also applied to the synthesis of compounds containing the boronic acid moiety. However, such applications have unique problems. Chief among them is the issue of copper-mediated boronic acid degradation in copper-assisted [2,3]-cycloadditions involving an alkyne and an azido compound as the starting materials. This review summarizes recent developments, analyzes potential issues, and discusses known as well as possible solutions.

Keywords: Click chemistry; CuAAC; Boronic acids

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