Organic Chemistry

Catalytic Deoxygenative Coupling of Aromatic Esters with Organophosphorus Compounds

Junichiro Yamaguchi Waseda University


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 as a bifunctional catalyst to activate the acyl C–O bond of the ester and to support the reduction with sodium formate.


Thumbnail image of BBisshikideoxygenative200312final.pdf
download asset BBisshikideoxygenative200312final.pdf 0.91 MB [opens in a new tab]

Supplementary material

Thumbnail image of SI_Kurosawa_isshiki20200312final.pdf
download asset SI_Kurosawa_isshiki20200312final.pdf 26 MB [opens in a new tab]
SI Kurosawa isshiki20200312final