Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides

Mieko Arisawa; Toru Yamada; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2010.07.038

Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides

Mieko Arisawa, Toru Yamada, Masahiko Yamaguchi

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

16 Citations (Scopus)

Abstract

A rhodium complex catalyzed the reaction of acid fluorides and tetraethyldiphosphine disulfide giving acylphosphine sulfides. Aromatic acid fluorides with electron donating p-groups reacted smoothly giving the products in high yields. Aliphatic acid fluorides with secondary and tertiary a-carbons were also converted to alkanoylphosphine sulfides, whereas the reaction of a substrate with an α-methylene carbon was accompanied by enol ester formation.

Original language	English
Pages (from-to)	4957-4958
Number of pages	2
Journal	Tetrahedron Letters
Volume	51
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.038
Publication status	Published - 2010
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2010.07.038

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abstract = "A rhodium complex catalyzed the reaction of acid fluorides and tetraethyldiphosphine disulfide giving acylphosphine sulfides. Aromatic acid fluorides with electron donating p-groups reacted smoothly giving the products in high yields. Aliphatic acid fluorides with secondary and tertiary a-carbons were also converted to alkanoylphosphine sulfides, whereas the reaction of a substrate with an α-methylene carbon was accompanied by enol ester formation.",

author = "Mieko Arisawa and Toru Yamada and Masahiko Yamaguchi",

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

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T1 - Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides

AU - Arisawa, Mieko

AU - Yamada, Toru

AU - Yamaguchi, Masahiko

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

PY - 2010

Y1 - 2010

N2 - A rhodium complex catalyzed the reaction of acid fluorides and tetraethyldiphosphine disulfide giving acylphosphine sulfides. Aromatic acid fluorides with electron donating p-groups reacted smoothly giving the products in high yields. Aliphatic acid fluorides with secondary and tertiary a-carbons were also converted to alkanoylphosphine sulfides, whereas the reaction of a substrate with an α-methylene carbon was accompanied by enol ester formation.

AB - A rhodium complex catalyzed the reaction of acid fluorides and tetraethyldiphosphine disulfide giving acylphosphine sulfides. Aromatic acid fluorides with electron donating p-groups reacted smoothly giving the products in high yields. Aliphatic acid fluorides with secondary and tertiary a-carbons were also converted to alkanoylphosphine sulfides, whereas the reaction of a substrate with an α-methylene carbon was accompanied by enol ester formation.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides

Abstract

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