通过远程杂芳基迁移由二氧化硫生成杂芳基取代的磺酰化合物。
Generation of Heteroaryl-Substituted Sulfonyl Compounds from Sulfur Dioxide via Remote Heteroaryl -Migration.
作者信息
Yang Man, Chang Xiaotong, Ye Shengqing, Ding Qiuping, Wu Jie
机构信息
Key Laboratory for Green Chemistry of Jiangxi Province, Key Laboratory of Functional Small Molecules for Ministry of Education, Jiangxi Normal University, 99 Ziyang Avenue, Nanchang 330022, China.
SchooSchool of Pharmaceutical and Materials Engineering & Institute for Advanced Studies, Taizhou University, 1139 Shifu Avenue, Taizhou 318000, China.
出版信息
J Org Chem. 2021 Nov 5;86(21):15177-15184. doi: 10.1021/acs.joc.1c01778. Epub 2021 Oct 12.
The generation of heteroaryl-substituted sulfonyl compounds via a catalyst-, base-, and additive-free three-component reaction of heteroaryl-substituted tertiary alcohols, aryldiazonium tetrafluoroborates, and DABCO·(SO) under mild conditions is developed. Various functional groups are tolerated well in this transformation, and a broad substrate scope is demonstrated. A preliminary mechanistic investigation shows that this reaction undergoes a radical process, including the insertion of sulfur dioxide, sulfonyl radical addition to unactivated alkene, and remote heteroaryl -migration.
通过在温和条件下杂芳基取代的叔醇、芳基四氟硼酸重氮盐和DABCO·(SO)的无催化剂、无碱和无添加剂的三组分反应，开发了杂芳基取代的磺酰化合物的生成方法。在该转化过程中，各种官能团都能很好地耐受，并展示了广泛的底物范围。初步机理研究表明，该反应经历自由基过程，包括二氧化硫的插入、磺酰基自由基加成到未活化的烯烃以及远程杂芳基迁移。
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