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

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 th...

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Published inOrganic letters Vol. 23; no. 5; pp. 1582 - 1587
Main Authors Kanemoto, Kazuya, Furuhashi, Koudai, Morita, Yoshitsugu, Komatsu, Teruyuki, Fukuzawa, Shin-ichi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 05.03.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SULFIDES
THIOCYANOGEN CHLORIDE
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Summary: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.
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c04289