Hexafluoroisopropanol-Enabled Copper-Catalyzed Asymmetric Halogenation of Cyclic Diaryliodoniums for the Synthesis of Axially Chiral 2,2′-Dihalobiaryls
Jie Ke, Bing Zu, Yonghong Guo, Yingzi Li, Chuan He
Abstract
An efficient asymmetric halogenation of cyclic diaryliodonium salts is demonstrated, which gives access to a wide range of axially chiral 2,2'-dihalobiaryls in good to excellent yields and with excellent enantioselectivities. The use of CuX with chiral bisoxazoline ligand and tetrabutylammonium halides in the unique solvent of hexafluoroisopropanol (HFIP) led to the best results in the process. The axially chiral 2,2'-dihalobiaryls can be transformed into a number of enantiopure chiral ligands that could be potentially useful in asymmetric catalysis.
Topics & Concepts
Enantiopure drugChemistryHalogenationHalideAxial symmetryCatalysisCombinatorial chemistrySolventLigand (biochemistry)Chiral ligandCopperEnantioselective synthesisOrganic chemistryMathematicsReceptorGeometryBiochemistryAxial and Atropisomeric Chirality SynthesisAlkaloids: synthesis and pharmacologyAsymmetric Synthesis and Catalysis