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

13 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

Access to Document

10.1016/j.tetlet.2011.02.112

Cite this

@article{5c12014f1d394b358240bdce24766152,

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. ",

year = "2011",

month = may,

day = "4",

doi = "10.1016/j.tetlet.2011.02.112",

language = "English",

volume = "52",

pages = "2410--2412",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "18",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=79953267163&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=79953267163&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.02.112

DO - 10.1016/j.tetlet.2011.02.112

M3 - Article

AN - SCOPUS:79953267163

VL - 52

SP - 2410

EP - 2412

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 18

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this