Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

被引:50
作者
Bao, Hanyang [1 ]
Zhou, Bingwei [1 ]
Jin, Hongwei [1 ]
Liu, Yunkui [1 ]
机构
[1] Zhejiang Univ Technol, Coll Chem Engn, State Key Lab Breeding Base Green Chem Synth Tech, Hangzhou 310014, Zhejiang, Peoples R China
关键词
REGIOSELECTIVE SYNTHESIS; OXIDATIVE CYCLIZATION; ANTINEOPLASTIC AGENTS; CELL-GROWTH; CIS-ALKENES; PALLADIUM; REDUCTION; WATER; GENERATION; TUBULIN;
D O I
10.1021/acs.joc.9b00321
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We herein describe a B(2)Pin(2)-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(2) in a high deuteration ratio by using readily available ethanol-d(1) as the deuterium source.
引用
收藏
页码:3579 / 3589
页数:11
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