Visible-Light-Promoted Cross-Coupling Reactions of Aryldiazonium Salts with <i>S</i>-Methyl-<i>d</i><sub>3</sub> Sulfonothioate or <i>Se</i>-Methyl-<i>d</i><sub>3</sub> Selenium Sulfonate: Synthesis of Trideuteromethylated Sulfides, Sulfoxides, and Selenides
Cheng-Mi Huang, Jian Li, Jing-Jing Ai, Xinyu Liu, Weidong Rao, Shun‐Yi Wang
Abstract
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.
Topics & Concepts
ChemistryDeuteriumPhotocatalysisVisible spectrumMethyl groupPhotochemistryGroup (periodic table)Organic chemistryCatalysisOptoelectronicsPhysicsQuantum mechanicsChemical Reactions and IsotopesSulfur-Based Synthesis TechniquesRadical Photochemical Reactions