金的氧化还原催化作用，使用硒阳离子作为温和氧化剂。
Gold Redox Catalysis with a Selenium Cation as a Mild Oxidant.
机构信息
College of Chemistry, Chemical Engineering and Material Science, Shandong Normal University, Jinan, Shandong, 250014, P. R. China.
Department of Chemistry, University of South Florida, Tampa, FL, 33620, USA.
出版信息
Chemistry. 2020 May 12;26(27):5946-5950. doi: 10.1002/chem.202000166. Epub 2020 Apr 14.
Abstract
Gold-catalyzed alkyne and allene diselenations were developed. Excellent regioselectivity (trans) and good to excellent yields were achieved (up to 98 % with 2 % catalyst loading) with a wide range of substrates. Mechanistic investigation revealed the formation of a vinyl gold(I) intermediate followed by an intermolecular selenium cation migration, suggesting that a gold(I/III) redox process was successfully implemented under mild conditions.
摘要
发展了金催化的炔烃和丙二烯二硒化反应。该反应具有优异的区域选择性（反式）和良好至优秀的产率（在 2%的催化剂负载下高达 98%），底物适用范围广泛。机理研究表明，该反应首先形成乙烯基金（I）中间体，然后进行分子间硒阳离子迁移，这表明在温和条件下成功实施了金（I/III）氧化还原过程。
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2
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Chem Sci. 2019 Jul 31;10(36):8411-8420. doi: 10.1039/c9sc02372k. eCollection 2019 Sep 28.
3
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