通过炔基硫醚的无金属氧化环化合成异硫代色满-3-酮。
Synthesis of Isothiochroman-3-ones via Metal-Free Oxidative Cyclization of Alkynyl Thioethers.
作者信息
Zhang Ying-Qi, Zhu Xin-Qi, Chen Yang-Bo, Tan Tong-De, Yang Ming-Yang, Ye Long-Wu
机构信息
iChEM, State Key Laboratory of Physical Chemistry of Solid Surfaces and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering , Xiamen University , Xiamen 361005 , China.
State Key Laboratory of Organometallic Chemistry , Chinese Academy of Sciences , Shanghai 200032 , China.
出版信息
Org Lett. 2018 Dec 7;20(23):7721-7725. doi: 10.1021/acs.orglett.8b03462. Epub 2018 Nov 16.
A novel Brønsted acid-catalyzed oxidative C-H functionalization of alkynyl thioethers has been developed. This method allows the practical synthesis of valuable isothiochroman-3-ones in mostly moderate to good yields under mild reaction conditions and features a broad substrate scope and wide functional group tolerance. Moreover, this metal-free oxidation can also be used to promote formal N-H insertion involving an unexpected 1,2-sulfur migration, affording useful 1,4-benzothiazin-3-ones.
已开发出一种新型布朗斯特酸催化的炔基硫醚氧化C-H官能团化反应。该方法能够在温和的反应条件下，以大多中等至良好的产率实际合成有价值的异硫代苯并二氢吡喃-3-酮，具有广泛的底物范围和良好的官能团耐受性。此外，这种无金属氧化反应还可用于促进涉及意外1,2-硫迁移的形式上的N-H插入反应，得到有用的1,4-苯并噻嗪-3-酮。
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