Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

Ryota Isshiki; Kei Muto; Junichiro Yamaguchi

doi:10.1021/acs.orglett.8b00080

Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

Ryota Isshiki, Kei Muto, Junichiro Yamaguchi^*

^*Corresponding author for this work

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

78 Citations (Scopus)

Abstract

Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.

Original language	English
Pages (from-to)	1150-1153
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.8b00080
Publication status	Published - 2018 Feb 16

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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title = "Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds",

abstract = "Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.",

author = "Ryota Isshiki and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H01011, JP16H04148 (to J.Y.), and JP17K14453, the Early Bird Program of Waseda University, and JXTG Energy for Young Researchers (to K.M.). We thank Mr. Ryosuke Takise (Nagoya University) for the measurement of HRMS. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.orglett.8b00080",

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T1 - Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

AU - Isshiki, Ryota

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Nos. JP16H01011, JP16H04148 (to J.Y.), and JP17K14453, the Early Bird Program of Waseda University, and JXTG Energy for Young Researchers (to K.M.). We thank Mr. Ryosuke Takise (Nagoya University) for the measurement of HRMS. Publisher Copyright: © 2018 American Chemical Society.

PY - 2018/2/16

Y1 - 2018/2/16

N2 - Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.

AB - Ni-catalyzed C-P bond formation was achieved using aromatic esters as unconventional aryl sources. The key to success was the use of a thiophene-based diphosphine ligand (dcypt). Several aromatic esters including heteroaromatics can be coupled with phosphine oxides and phosphates, providing aryl phosphorus compounds. The synthetic utility of the method was demonstrated by application of the present protocol to the sequential coupling reactions.

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JO - Organic Letters

JF - Organic Letters

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Decarbonylative C-P bond formation using aromatic esters and organophosphorus compounds

Abstract

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