Acid-Mediated Sulfonylthiolation of Arenes via Selective Activation of SS-Morpholino Dithiosulfonate

Kazuya Kanemoto, Koudai Furuhashi, Yoshitsugu Morita, Teruyuki Komatsu, Shin Ichi Fukuzawa

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


A trifluoroacetic-acid-mediated desulfurilative sulfonylthiolation of arenes using SS-morpholino dithiosulfonate is described. This system is based on selective activation of the morpholino group over the tosyl group of the doubly transformable sulfur surrogate. Mechanistic studies suggested that the reaction proceeds through electrophilic aromatic substitution followed by sulfur extrusion. The wide substrate scope of this reaction and the transformability of the resulting thiosulfonates enable expeditious access to divergent multifunctionalized sulfides.

Original languageEnglish
Pages (from-to)1582-1587
Number of pages6
JournalOrganic letters
Issue number5
Publication statusPublished - 2021 Mar 5
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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