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可见光促进芳基重氮盐与α-甲基硫代磺酸酯或α-甲基硒磺酸酯的交叉偶联反应:三氘代甲基化硫醚、亚砜和硒醚的合成

Visible-Light-Promoted Cross-Coupling Reactions of Aryldiazonium Salts with -Methyl- Sulfonothioate or -Methyl- Selenium Sulfonate: Synthesis of Trideuteromethylated Sulfides, Sulfoxides, and Selenides.

作者信息

Huang Cheng-Mi, Li Jian, Ai Jing-Jing, Liu Xin-Yu, Rao Weidong, Wang Shun-Yi

机构信息

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

Nanjing Forest University, Nanjing 210037, China.

出版信息

Org Lett. 2020 Nov 20;22(22):9128-9132. doi: 10.1021/acs.orglett.0c03562. Epub 2020 Nov 4.

DOI:10.1021/acs.orglett.0c03562
PMID:33147971
Abstract

A novel visible-light-photocatalytic deuterated thiomethylation/methylselenation of aryldiazonium salts utilizing /methyl- sulfonothioate has been developed. The mild conditions and the various functional groups provide a green protocol for the efficient and rapid introduction of the -CD or -CD group with useful levels of deuterium content (>91% D). Trideuteromethyl sulfoxides have also been successfully chemoselectively observed by simple atmospheric changes under photocatalytic conditions.

摘要

已开发出一种利用甲基硫代磺酸酯对芳基重氮盐进行新型可见光光催化氘代硫甲基化/甲基硒化反应。温和的条件和各种官能团为高效快速引入具有有用氘含量(>91%D)的-CD或-CD基团提供了一种绿色方案。在光催化条件下,通过简单的大气变化也成功地化学选择性地观察到了三氘代甲基亚砜。

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Visible-Light-Promoted Cross-Coupling Reactions of Aryldiazonium Salts with -Methyl- Sulfonothioate or -Methyl- Selenium Sulfonate: Synthesis of Trideuteromethylated Sulfides, Sulfoxides, and Selenides.可见光促进芳基重氮盐与α-甲基硫代磺酸酯或α-甲基硒磺酸酯的交叉偶联反应:三氘代甲基化硫醚、亚砜和硒醚的合成
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