Direct transformation of organosulfur compounds to organophosphorus compounds: Rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides

Mieko Arisawa; Takuya Watanabe; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2011.02.112

Direct transformation of organosulfur compounds to organophosphorus compounds: Rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides

Mieko Arisawa, Takuya Watanabe, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

14 Citations (Scopus)

Abstract

A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh₃)₄ and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides.

Original language	English
Pages (from-to)	2410-2412
Number of pages	3
Journal	Tetrahedron Letters
Volume	52
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2011.02.112
Publication status	Published - 2011 May 4

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2011.02.112

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title = "Direct transformation of organosulfur compounds to organophosphorus compounds: Rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides",

abstract = "A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh3)4 and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides.",

author = "Mieko Arisawa and Takuya Watanabe and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by Grant-in-Aid for Scientific Research ( No. 21229001 ), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks for financial support from the Grant-in-Aid for Scientific Research from MEXT ( No. 22689001 ) and also to the Naito Foundation. ",

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T1 - Direct transformation of organosulfur compounds to organophosphorus compounds

T2 - Rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides

AU - Arisawa, Mieko

AU - Watanabe, Takuya

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by Grant-in-Aid for Scientific Research ( No. 21229001 ), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks for financial support from the Grant-in-Aid for Scientific Research from MEXT ( No. 22689001 ) and also to the Naito Foundation.

PY - 2011/5/4

Y1 - 2011/5/4

N2 - A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh3)4 and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides.

AB - A rhodium-catalyzed method for the synthesis of organophosphorus compounds directly from organosulfur compounds was developed. In the presence of RhH(PPh3)4 and depe, the reaction of 1-alkylthioalkynes with tetraethyldiphosphine disulfide gave 1-alkynylphosphine sulfides. The same complex catalyzed the reaction of thioesters giving acylphosphine sulfides.

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Direct transformation of organosulfur compounds to organophosphorus compounds: Rhodium-catalyzed synthesis of 1-alkynylphosphine sulfides and acylphosphine sulfides

Abstract

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