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

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

doi:10.1021/acs.orglett.0c04289

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 journal › Article › peer-review

4 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	1582-1587
Number of pages	6
Journal	Organic letters
Volume	23
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.0c04289
Publication status	Published - 2021 Mar 5
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Acid-Mediated Sulfonylthiolation of Arenes via Selective Activation of SS-Morpholino Dithiosulfonate",

abstract = "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. ",

author = "Kazuya Kanemoto and Koudai Furuhashi and Yoshitsugu Morita and Teruyuki Komatsu and Fukuzawa, {Shin Ichi}",

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T1 - Acid-Mediated Sulfonylthiolation of Arenes via Selective Activation of SS-Morpholino Dithiosulfonate

AU - Kanemoto, Kazuya

AU - Furuhashi, Koudai

AU - Morita, Yoshitsugu

AU - Komatsu, Teruyuki

AU - Fukuzawa, Shin Ichi

N1 - Funding Information: This work was supported by the Kato Memorial Bioscience Foundation (K.K.), JSPS KAKENHI grant numbers JP19K23637 (Research Activity Start-up; K.K.) and JP20K15288 (Young Scientists; K.K.), and The Institute of Science and Engineering, Chuo University. Publisher Copyright: ©

PY - 2021/3/5

Y1 - 2021/3/5

N2 - 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.

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

Abstract

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