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丙烯酰胺的五氟硫烷基化反应:用SFCl合成含SF的异喹啉二酮

Pentafluorosulfanylation of Acrylamides: The Synthesis of SF-Containing Isoquinolinediones with SFCl.

作者信息

Tan Xinqiang, Li Yuezhen, Hao Ziyou, Wang Jia, Liu Xiangqian, Liu Bingqing, Yuan Jianmei, Fang Lizhen, Zhou Ping-Xin, Wang Yingling

机构信息

School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.

School of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, P. R. China.

出版信息

J Org Chem. 2024 Nov 1;89(21):15941-15952. doi: 10.1021/acs.joc.4c02181. Epub 2024 Oct 24.

Abstract

We disclose herein an efficient and facile method for the synthesis of SF-containing isoquinolinediones with an all-carbon quaternary stereocenter via intramolecular pentafluorosulfanylation of acrylamides using SFCl as a pentafluorosulfanylation reagent. The protocol proceeds under mild reaction conditions and enjoys a broad substrate scope, wide functional group compatibility, and high atom- and step-economy. A radical mechanism involving the SF radical cascade addition/cyclization of acrylamides is proposed.

摘要

我们在此公开了一种高效简便的方法,以SFCl作为五氟硫烷基化试剂,通过丙烯酰胺的分子内五氟硫烷基化反应合成具有全碳季碳立体中心的含SF异喹啉二酮。该方法在温和的反应条件下进行,具有广泛的底物范围、良好的官能团兼容性以及高原子经济性和步骤经济性。我们提出了一种涉及丙烯酰胺的SF自由基级联加成/环化的自由基机理。

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