Regioselective C–H alkynylation with haloalkynes enabled by nitrogen functionalities via Rh catalysis†

Qiaoya Zhang , Bifu Liu , Ci Chen , Yinling Li , Kejun Feng , Sheng Hu , Yang Gao , Yanping Huo , Qian Chen , Xianwei Li
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Abstract

Regioselective introduction of the versatile alkyne functionality would enable rapid construction of molecular complexity; however, sterically hindered silyl-containing alkynylation reagents are typically required, thus, hampering further applications. Herein, we have developed a transformable nitrogen functionality-enabled regioselective C–H alkynylation cascade with aliphatic haloalkynes, furnishing alkynes and heterocycles, which thus facilitated concise synthesis of CB2 receptor agonist and protein kinase inhibitor analogues.

Abstract Image

氮官能团激活的C-H与卤代烷的区域选择性烷基化
区域选择性引入多功能化炔可以快速构建复杂分子,然而,通常需要空间位阻的含硅烷基烷基化试剂,因此,阻碍了进一步的应用。在此,我们开发了可转换的氮功能,使C-H炔基化与脂肪族卤代炔、供给炔和杂环级联,从而促进了CB2受体激动剂、蛋白激酶抑制剂类似物的简明传递。
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CiteScore
7.80
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