Nickel-Catalyzed Atroposelective Cross-Electrophile Coupling of Aryl Halides: A General and Practical Route to Diverse MOP-Type Ligands
Raphael S. Kim, Lebogang O. Kgoadi, Jacob C. Hayes, Derek Rainboth, Catherine M. Mudd, Glenn P. A. Yap, Donald A. Watson
Abstract
We report a highly cross- and atroposelective coupling between ortho -(chloro)arylphosphine oxides and ortho -(bromo)aryl ethers. This previously unknown asymmetric nickel-catalyzed reaction offers a direct route to highly enantioenriched axially chiral biaryl monophosphine oxides that are difficult to access by other means. These products can be readily reduced to generate chiral MOP-type ligands bearing complex skeletal backbones. The utility of these chiral ligands in asymmetric catalysis is also demonstrated.
Topics & Concepts
ChemistryElectrophileArylNickelHalideCatalysisCombinatorial chemistryCoupling (piping)Medicinal chemistryOrganic chemistryAlkylEngineeringMechanical engineeringAxial and Atropisomeric Chirality SynthesisMolecular spectroscopy and chiralityAsymmetric Synthesis and Catalysis