State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering , Zhejiang University of Technology , Hangzhou 310014 , People's Republic of China.
J Org Chem. 2019 Mar 15;84(6):3579-3589. doi: 10.1021/acs.joc.9b00321. Epub 2019 Mar 1.
We herein describe a BPin-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4- d in a high deuteration ratio by using readily available ethanol- d as the deuterium source.
我们在此描述了一种 BPin 辅助的铜催化炔烃半氢化反应。在温和的反应条件下，多种烯烃以良好到优异的收率和 Z 选择性得到。机理研究表明，该反应涉及转移氢化过程，乙醇在反应中既是溶剂又是氢供体。通过使用易得的乙醇- d 作为氘源，本方法可以方便地合成氘代 Z-烯烃，如 Z-康普瑞汀 A4-d，具有较高的氘代比。
