TY - JOUR
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.
Publisher Copyright:
© 2020 American Chemical Society.
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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U2 - 10.1021/jacs.0c02839
DO - 10.1021/jacs.0c02839
M3 - Article
C2 - 32279494
AN - SCOPUS:85083824228
VL - 142
SP - 7386
EP - 7392
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 16
ER -