Axially Chiral Biaryl Monophosphine Oxides Enabled by Palladium/WJ-Phos-Catalyzed Asymmetric Suzuki–Miyaura Cross-coupling
Wangqin Ji, Haihong Wu, Junliang Zhang
Abstract
A highly enantioselective palladium/WJ-Phos-catalyzed Suzuki–Miyaura coupling reaction for efficient construction of axially chiral biaryl monophosphine oxides was developed. A series of axially chiral biaryl monophosphine oxides were obtained in good yields and with high enantioselectivities. The practicability of this reaction was validated in the straightforward synthesis of axially chiral biaryl monophosphine ligand and demonstrated by a 100-g-scale synthesis. Moreover, various functionalizations of the product make it as a platform molecule for synthesis of other chiral biaryl phosphines.
Topics & Concepts
PalladiumAxial symmetryCombinatorial chemistryCatalysisChemistryEnantioselective synthesisLigand (biochemistry)Coupling reactionCoupling (piping)Organic chemistryMaterials scienceReceptorPhysicsQuantum mechanicsBiochemistryMetallurgyAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityChemical synthesis and alkaloids