Journal of the American Chemical Society · 2020 · 46 citations · 62 references
Natural SciencesChemistryCatalysisOrganic ChemistryOrganometallic ChemistryCatalytic MechanismsOrganic SynthesisOrganophosphate CompoundsPalladium CatalystsPalladium-catalyzed Cross-coupling
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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Decarbonylative organoboron cross-coupling of esters by nickel catalysis
Kei Muto, Junichiro Yamaguchi, Djamaladdin G. Musaev et al. · Nature Communications · 2015 · 281 citations · Full text