Yu Ying, Liebeskind Lanny S
Emory University, Department of Chemistry, 1515 Dickey Drive, Atlanta, Georgia 30322, USA.
J Org Chem. 2004 May 14;69(10):3554-7. doi: 10.1021/jo049964p.
Thiol esters and B-alkyl-9-BBN derivatives couple in the presence of a copper(I) carboxylate mediator and a palladium catalyst. In contrast to copper-mediated, palladium-catalyzed cross-couplings of thioorganics with boronic acids, the current coupling reaction of 9-BBN derivatives is facilitated by the addition of a base such as Cs(2)CO(3). Under optimized conditions, a variety of thiol esters react with different B-alkyl-9-BBN derivatives giving ketones in moderate to excellent yields.
硫醇酯与β-烷基-9-硼双环壬烷衍生物在羧酸亚铜(I)介导剂和钯催化剂存在下发生偶联反应。与铜介导、钯催化的硫代有机物与硼酸的交叉偶联反应不同,9-硼双环壬烷衍生物的当前偶联反应通过添加碱(如碳酸铯)得以促进。在优化条件下,多种硫醇酯与不同的β-烷基-9-硼双环壬烷衍生物反应,以中等至优异的产率生成酮类化合物。