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钯催化芳基和杂芳基三氟硼酸钾的铃木-宫浦交叉偶联反应

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates.

作者信息

Molander Gary A, Biolatto Betina

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia 19104-6323, USA.

出版信息

J Org Chem. 2003 May 30;68(11):4302-14. doi: 10.1021/jo0342368.

Abstract

An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl(2)(dppf).CH(2)Cl(2) efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.

摘要

本文介绍了芳基和杂芳基三氟硼酸钾在铃木-宫浦交叉偶联反应中反应活性的扩展研究。芳基和富电子杂芳基三氟硼酸盐与芳基和活性杂芳基溴化物的偶联在无配体条件下很容易进行。当钝化的芳基和杂芳基三氟硼酸盐与芳基和杂芳基溴化物及氯化物偶联时,低负载量(0.5 - 2%)的PdCl₂(dppf)·CH₂Cl₂能有效催化反应。在这两种条件下,反应通常都可以在开放大气环境中进行。

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