Copper-catalysed, diboron-mediated cis-dideuterated semihydrogenation of alkynes with heavy water

被引：31

作者：

Han, Xiaowei ^{[1
,2
]}

Hu, Jiefeng ^{[1
]}

Chen, Cheng ^{[1
]}

Yuan, Yu ^{[2
]}

Shi, Zhuangzhi ^{[1
]}

机构：

[1] Nanjing Univ, Sch Chem & Chem Engn, State Key Lab Coordinat Chem, Nanjing 210093, Jiangsu, Peoples R China

[2] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Jiangsu, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 48期

基金：

中国国家自然科学基金;

关键词：

TRANSITION-METAL-FREE; STEREOSELECTIVE-SYNTHESIS; DEUTERIUM-OXIDE; GOLD CATALYST; DEUTERATION; BORYLATION; TRITIATION; ALKENES; OZONOLYSIS; EXCHANGE;

D O I：

10.1039/c9cc03213d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Methods to incorporate deuterium atoms into organic molecules are valuable for the pharmaceutical industry. Here, we found that diboron reagents can efficiently mediate the transfer of two D atoms from heavy water directly onto alkynes through copper-catalysed cis-selective semihydrogenation. Avoiding the use of costly and flammable D2 gas, this safe and practical process can proceed with excellent chemoselectivity and stereoselectivity. Utilizing the present method as the key step, the formal asymmetric total synthesis of d2-deuterium-labeled cis-combretastatin A4 is demonstrated. Mechanistic studies suggest that monoborylation of alkynes is the key step for this semihydrogenation process.

引用

页码：6922 / 6925

页数：4