氟磺酰脒可实现1,5-二取代四唑的模块化合成。
-Fluorosulfurylamidines Enable Modular Synthesis of 1,5-Disubstituted Tetrazoles.
作者信息
Li Xixi, Wang Tianyu, Xu Long, Dong Jiajia
机构信息
Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
Institute of Translational Medicine, National Facility for Translational Medicine (Shanghai), Shanghai Jiao Tong University, Shanghai 200240, China.
出版信息
Org Lett. 2024 Nov 1;26(43):9395-9400. doi: 10.1021/acs.orglett.4c03687. Epub 2024 Oct 24.
Here we report the modular synthesis of 1,5-disubstituted tetrazoles using two highly chemoselective reactions, ligations of -fluorosulfurylamidines with amines and diazotransfer reactions between FSON and -monosubstituted amidines, respectively. Enabled by sulfur(VI) fluoride exchange (SuFEx) click chemistry, we have successfully synthesized a series of -fluorosulfurylamidines and identified them as stable and scalable organic synthons. We then discover that -fluorosulfurylamidines react selectively toward a series of aliphatic amines, resulting in the formation of -monosubstituted amidines that can react further with FSON to deliver 1,5-disubstituted tetrazoles. Our work provides a new platform for generating a library of 1,5-disubstituted tetrazoles with diverse structures, which is unprecedented.
在此，我们报道了使用两种高度化学选择性反应对1,5-二取代四唑进行模块化合成，即分别使氟磺酰亚胺与胺进行连接反应，以及使氟磺酰亚胺（FSON）与单取代亚胺之间发生重氮转移反应。借助六价硫氟交换（SuFEx）点击化学，我们成功合成了一系列氟磺酰亚胺，并将它们鉴定为稳定且可扩展的有机合成子。然后我们发现，氟磺酰亚胺对一系列脂肪族胺具有选择性反应，生成的单取代亚胺可进一步与氟磺酰亚胺（FSON）反应生成1,5-二取代四唑。我们的工作为生成具有多样结构的1,5-二取代四唑文库提供了一个全新的平台，这是前所未有的。
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