Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

Mieko Arisawa; Tomohiro Kubota; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2008.01.109

Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

Mieko Arisawa, Tomohiro Kubota, Masahiko Yamaguchi

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

The Wilkinson complex RhCl(PPh₃)₃ catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh₃)₃ (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide.

Original language	English
Pages (from-to)	1975-1978
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	12
DOIs	https://doi.org/10.1016/j.tetlet.2008.01.109
Publication status	Published - Mar 17 2008
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.01.109

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title = "Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide",

abstract = "The Wilkinson complex RhCl(PPh3)3 catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)3 (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide.",

author = "Mieko Arisawa and Tomohiro Kubota and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by JSPS (Nos. 16109001 and 17689001). M.A. expresses her thanks to the Grant-in-Aid for Scientific Research on Priority Areas, {\textquoteleft}Advanced Molecular Transformations of Carbon Resources{\textquoteright} from MEXT (Nos. 18037005 and 19020008). ",

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T1 - Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

AU - Arisawa, Mieko

AU - Kubota, Tomohiro

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by JSPS (Nos. 16109001 and 17689001). M.A. expresses her thanks to the Grant-in-Aid for Scientific Research on Priority Areas, ‘Advanced Molecular Transformations of Carbon Resources’ from MEXT (Nos. 18037005 and 19020008).

PY - 2008/3/17

Y1 - 2008/3/17

N2 - The Wilkinson complex RhCl(PPh3)3 catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)3 (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide.

AB - The Wilkinson complex RhCl(PPh3)3 catalyzes equilibrating alkylthio exchange reaction of thioesters with disulfides. The treatment of a thioester and a dialkyl disulfide in refluxing diethyl ketone in the presence of RhCl(PPh3)3 (2.5 mol %) for 1.5 h gave an alkylthio exchanged thioester. The reaction of S-methyl ester was conducted shifting the equilibrium by removing volatile dimethyl disulfide.

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DO - 10.1016/j.tetlet.2008.01.109

M3 - Article

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SN - 0040-4039

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SP - 1975

EP - 1978

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 12

ER -

Rhodium-catalyzed alkylthio exchange reaction of thioester and disulfide

Abstract

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