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通过选择性 C-N 键断裂解锁酰胺:烯丙基溴介导的含氮官能团的发散合成。

Unlocking Amides through Selective C-N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups.

机构信息

Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 80708, Taiwan, ROC.

Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung 80708, Taiwan, ROC.

出版信息

Org Lett. 2021 Dec 17;23(24):9419-9424. doi: 10.1021/acs.orglett.1c03541. Epub 2021 Nov 16.

DOI:10.1021/acs.orglett.1c03541
PMID:34784227
Abstract

We report a new set of reactions based on the unlocking of amides through simple treatment with allyl bromide, creating a common platform for accessing a diverse range of nitrogen-containing functional groups such as primary amides, sulfonamides, primary amines, -acyl compounds (esters, thioesters, amides), and -sulfonyl esters. The method has potential industrial applicability, as demonstrated through gram-scale syntheses in batch and in a continuous flow system.

摘要

我们报告了一组新的反应,这些反应是通过简单地用烯丙基溴处理酰胺的开环反应得到的,为获得各种含氮官能团(如伯酰胺、磺胺、伯胺、-酰基化合物(酯、硫酯、酰胺)和 - 磺酰酯)提供了一个通用的平台。该方法具有潜在的工业适用性,通过批量和连续流动系统中的克级合成得到了证明。

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