Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

Miki B. Kurosawa; Ryota Isshiki; Kei Muto; Junichiro Yamaguchi

doi:10.1021/jacs.0c02839

Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

Miki B. Kurosawa, Ryota Isshiki, Kei Muto, Junichiro Yamaguchi

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

2 Citations (Scopus)

Abstract

We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

Original language	English
Pages (from-to)	7386-7392
Number of pages	7
Journal	Journal of the American Chemical Society
Volume	142
Issue number	16
DOIs	https://doi.org/10.1021/jacs.0c02839
Publication status	Published - 2020 Apr 22

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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@article{02f3bf6634394a729a5d9a37769b48ec,

title = "Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds",

abstract = "We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate. ",

author = "Kurosawa, {Miki B.} and Ryota Isshiki and Kei Muto and Junichiro Yamaguchi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726 (to J.Y.), JP18H04661 (hybrid catalysis), and JP19K15573 (to K.M.). We thank Prof. Masahiro Terada (Tohoku University) for fruitful discussion about the reaction mechanism. The Materials Characterization Central Laboratory in Waseda University is acknowledged for the support of HRMS measurement.",

year = "2020",

month = apr,

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doi = "10.1021/jacs.0c02839",

language = "English",

volume = "142",

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journal = "Journal of the American Chemical Society",

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T1 - Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

AU - Kurosawa, Miki B.

AU - Isshiki, Ryota

AU - Muto, Kei

AU - Yamaguchi, Junichiro

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. JP19H02726 (to J.Y.), JP18H04661 (hybrid catalysis), and JP19K15573 (to K.M.). We thank Prof. Masahiro Terada (Tohoku University) for fruitful discussion about the reaction mechanism. The Materials Characterization Central Laboratory in Waseda University is acknowledged for the support of HRMS measurement.

PY - 2020/4/22

Y1 - 2020/4/22

N2 - We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

AB - We have developed a deoxygenative coupling of aromatic esters with diarylphosphine oxides/dialkyl phosphonates under palladium catalysis. In this reaction, aromatic esters can work as novel benzylation reagents to give the corresponding benzylic phosphorus compounds. The key of this reaction is the use of phenyl esters, an electron-rich diphosphine as a ligand, and sodium formate as a hydrogen source. Arylcarboxylic acids were also applicable in this reaction using (Boc)2O as an additive. Palladium/dcype worked to activate the acyl C-O bond of the ester and to support the reduction with sodium formate.

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