Visible-Light-Promoted Cross-Coupling Reactions of Aryldiazonium Salts with S‑Methyl‑d3 Sulfonothioate or Se-Methyl‑d3 Selenium Sulfonate: Synthesis of Trideuteromethylated Sulfides, Sulfoxides, and Selenides
Cheng-Mi Huang1, Jian Li1, Jing-Jing Ai1, Xin-Yu Liu1, Weidong Rao2, and Shun-Yi Wang1,*（汪顺义）
1Key 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
2Weidong Rao − Nanjing Forest University, Nanjing 210037
Org. Lett. 2020, 22, 9128--9132
A novel visible-light-photocatalytic deuterated thiomethylation/methylselenation of aryldiazonium salts utilizing S/Se-methyl-d3 sulfonothioate has been developed. The mild conditions and the various functional groups provide a green protocol for the efficient and rapid introduction of the S-CD3 or Se-CD3 group with useful levels of deuterium content (>91% D). Trideuteromethyl sulfoxides have also been successfully chemoselectively observed by simple atmospheric changes under photocatalytic conditions.