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氧气引发的末端烯烃向β-酮砜/砜的氧代磺酰化/磺酰化反应

Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones.

作者信息

Wang Yanjie, Zhao Yuhan, Cai Changqun, Wang Lingyun, Gong Hang

机构信息

The Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.

School of Materials Science and Engineering, Hunan Institute of Technology, Hengyang 421002, China.

出版信息

Org Lett. 2021 Nov 5;23(21):8296-8301. doi: 10.1021/acs.orglett.1c03049. Epub 2021 Oct 19.

Abstract

A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.

摘要

已开发出一种由双氧触发的未活化烯烃的氧磺酰化/磺酰化反应,以实现β-酮砜/砜的合成。有趣的是,当使用不同类型的化合物作为底物时,发现了多种反应机制,并得到了不同的产物。该反应在室温下、空气气氛中、无金属和催化剂的情况下以高原子效率进行。重要的是,作为概念验证,使用该方法以克级规模合成了一种生物活性分子。

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