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

PHA - Molecular Pharmaceutical Science

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

15 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

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2010.07.038

Cite this

@article{6520f60bc46d4762972875b8012e35a0,

title = "Synthesis of acylphosphine sulfides by rhodium-catalyzed reaction of acid fluorides and diphosphine disulfides",

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. ",

year = "2010",

doi = "10.1016/j.tetlet.2010.07.038",

language = "English",

volume = "51",

pages = "4957--4958",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "38",

}

TY - JOUR

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.

UR - http://www.scopus.com/inward/record.url?scp=77958505940&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77958505940&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.07.038

DO - 10.1016/j.tetlet.2010.07.038

M3 - Article

AN - SCOPUS:77958505940

SN - 0040-4039

VL - 51

SP - 4957

EP - 4958

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this