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双(三氟甲磺酰)亚胺促进的烯烃与磺酰肼的氢磺酰化反应:一种合成支链砜的方法。

A Bi(OTf)-Promoted Hydrosulfonylation of Alkenes with Sulfonyl Hydrazides: An Approach to Branched Sulfones.

作者信息

Zhou Zheng, Liu Qianqian, Huang Zhibin, Zhao Yingsheng

机构信息

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Suzhou 215123, China.

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453000, P. R. China.

出版信息

Org Lett. 2022 Jun 24;24(24):4433-4437. doi: 10.1021/acs.orglett.2c01657. Epub 2022 Jun 9.

Abstract

The Bi(OTf)-promoted hydrosulfonylation of alkenes with sulfonyl hydrazides to produce branched sulfones is reported, in which various branched sulfones (>40 examples) have been prepared in moderate to good yields. The gram-scale reaction and synthesis of the experimental inhibitor precursor showed the potential application. A preliminary mechanistic study revealed that double-bond migration to form the α,β-conjugated alkene is crucial for this transformation.

摘要

据报道,Bi(OTf)促进的烯烃与磺酰肼的氢磺酰化反应可生成支链砜,其中已制备了多种支链砜(>40个实例),产率中等至良好。克级反应及实验性抑制剂前体的合成显示了其潜在应用。初步机理研究表明,双键迁移形成α,β-共轭烯烃对该转化至关重要。

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