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铜催化的异酰胺与杂环卡宾硼烷的自由基选择性硼氢化反应。

Copper-catalyzed radical -selective hydroboration of ynamides with -heterocyclic carbene boranes.

作者信息

Wang Kefeng, Yu Qingzhen, Mao Wenli, Zheng Yuxin, Xu Jing, Wang Yukun

机构信息

Department of Pharmacology, School of Medicine, Southern University of Science and Technology, Shenzhen 518055, China.

Clinical Medical Research Center, Southern University of Science and Technology Hospital, Shenzhen 518055, China.

出版信息

iScience. 2022 Aug 17;25(9):104977. doi: 10.1016/j.isci.2022.104977. eCollection 2022 Sep 16.

Abstract

Vinylboron compounds are important compounds in organic chemistry and biology. In this communication, we developed a copper(I)-catalyzed, highly regio- and stereoselective radical -hydroboration of ynamides with -heterocyclic carbene (NHC)-ligated borane is reported, which leads to a series of -boryl enmides that can be conveniently transformed into various multi-substituted enamides. Further investigation showcased that our method is robust and scalable. The mechanism of this unique reaction is studied and discussed.

摘要

乙烯基硼化合物是有机化学和生物学中的重要化合物。在本通讯中,我们报道了一种铜(I)催化的、高度区域和立体选择性的烯酰胺与氮杂环卡宾(NHC)连接的硼烷的自由基硼氢化反应,该反应生成了一系列β-硼基烯酰胺,它们可以方便地转化为各种多取代烯酰胺。进一步的研究表明,我们的方法具有稳健性和可扩展性。对这一独特反应的机理进行了研究和讨论。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/50cf/9440302/cdd393159bc3/fx1.jpg

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