Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide

Mieko Arisawa; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2010.07.040

Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide

Mieko Arisawa, Masahiko Yamaguchi

PHA - Molecular Pharmaceutical Science

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

12 Citations (Scopus)

Abstract

Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh₃)₄ and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)₂ and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction.

Original language	English
Pages (from-to)	4840-4842
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	37
DOIs	https://doi.org/10.1016/j.tetlet.2010.07.040
Publication status	Published - 2010 Sept 15

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tetlet.2010.07.040

Cite this

@article{a8db7846e0aa4f1e8ea6185a471e4ba9,

title = "Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide",

abstract = "Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh3)4 and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)2 and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction.",

author = "Mieko Arisawa and Masahiko Yamaguchi",

note = "Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (Nos. 21229001 and 22689001 ), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks to the Naito Foundation. ",

year = "2010",

month = sep,

day = "15",

doi = "10.1016/j.tetlet.2010.07.040",

language = "English",

volume = "51",

pages = "4840--4842",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Limited",

number = "37",

}

TY - JOUR

T1 - Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide

AU - Arisawa, Mieko

AU - Yamaguchi, Masahiko

N1 - Funding Information: This work was supported by a Grant-in-Aid for Scientific Research (Nos. 21229001 and 22689001 ), the GCOE program, and the WPI Initiative from JSPS. M.A. expresses her thanks to the Naito Foundation.

PY - 2010/9/15

Y1 - 2010/9/15

N2 - Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh3)4 and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)2 and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction.

AB - Transition metal complexes catalyzed the dialkylphosphinothioation reaction of alcohols and phenols with tetraalkyldiphosphine disulfides in high yields. Phenols were reacted in the presence of RhH(PPh3)4 and 1,2-bis(dimethylphosphino)ethane under THF reflux, and alcohols with Pd(OAc)2 and 1,2-bis(diphenylphosphino)benzene under chlorobenzene reflux. Primary alcohols reacted faster than secondary alcohols under these conditions, and protected tyrosine and serine were phosphinothioated with minimal racemization. Tetraphenyldiphosphine dioxide also underwent the P-O bond formation reaction.

UR - http://www.scopus.com/inward/record.url?scp=77955852571&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77955852571&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.07.040

DO - 10.1016/j.tetlet.2010.07.040

M3 - Article

AN - SCOPUS:77955852571

SN - 0040-4039

VL - 51

SP - 4840

EP - 4842

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 37

ER -

Metal-catalyzed phosphinyl ester forming reaction of alcohols and phenols with diphosphine disulfides and a dioxide

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this