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Regioselective Thiol-yne Reaction of Thiol with ((Methyl-d 3 )sulfonyl)ethyne: Synthesis of (2-((Methyl-d 3 )sulfonyl)vinyl)sulfides.

Ji-Min CaoXin-Yu LiuWei-Dong RaoShu-Su ShenDaopeng ShengShun-Yi Wang
Published in: The Journal of organic chemistry (2023)
Herein, we have developed a new method for the synthesis of ((methyl-d 3 )sulfonyl)ethyne, which is cost-effective and environmentally friendly and can be synthesized at the gram level. As an ideal thiol-yne reagent, it can be reacted with various types of thiols to afford ( Z )- and ( E )-type vinyl sulfides under different conditions with high selectivity. In addition, it can complete the conformational transition from Z- to E-type products under suitable conditions, and can also carry out further derivatization smoothly. The deuterium content of all products was greater than 99%. The preliminary mechanistic studies support the visible light-mediated radical course, and herein provide a novel and efficient synthetic strategy for the direct introduction of deuterated methyl groups, enriching the methods for the construction of C-S bond-containing compounds.
Keyphrases
  • visible light
  • molecular dynamics
  • single molecule
  • high performance liquid chromatography
  • simultaneous determination
  • low cost
  • multidrug resistant
  • case control
  • electron transfer
  • gas chromatography