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
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.