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铜促进的铃木反应:在2-杂环硼酸酯中的应用。

Copper-facilitated Suzuki reactions: application to 2-heterocyclic boronates.

作者信息

Deng James Z, Paone Daniel V, Ginnetti Anthony T, Kurihara Hideki, Dreher Spencer D, Weissman Steven A, Stauffer Shaun R, Burgey Christopher S

机构信息

Department of Medicinal Chemistry, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486, USA.

出版信息

Org Lett. 2009 Jan 15;11(2):345-7. doi: 10.1021/ol802556f.

DOI:10.1021/ol802556f
PMID:19093828
Abstract

The palladium-catalyzed Suzuki-Miyaura reaction has been utilized as one of the most powerful methods for C-C bond formation. However, Suzuki reactions of electron-deficient 2-heterocyclic boronates generally give low conversions and remain challenging. The successful copper(I) facilitated Suzuki coupling of 2-heterocyclic boronates that is broad in scope is reported. Use of this methodology affords greatly enhanced yields of these notoriously difficult couplings. Furthermore, mechanistic investigations suggest a possible role of copper in the catalytic cycle.

摘要

钯催化的铃木-宫浦反应已被用作形成碳-碳键最有效的方法之一。然而,缺电子的2-杂环硼酸酯的铃木反应通常转化率较低,仍然具有挑战性。据报道,成功实现了铜(I)促进的范围广泛的2-杂环硼酸酯的铃木偶联反应。使用这种方法可大大提高这些极难进行的偶联反应的产率。此外,机理研究表明铜在催化循环中可能发挥作用。

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