Ligand-Accelerated Stereoretentive Suzuki-Miyaura Coupling of Unprotected 3,3'-Dibromo-BINOL

J Org Chem. 2016 Feb 5;81(3):745-50. doi: 10.1021/acs.joc.5b02368. Epub 2016 Jan 15.

Abstract

An efficient synthesis of the enantiomerically pure 3,3'-bis-arylated BINOL derivatives is accomplished through the palladium-catalyzed Suzuki-Miyaura coupling of the unprotected 3,3'-dibromo-BINOL with complete retention of enantiopurity. The active catalyst system Pd(OAc)2/BI-DIME has enabled mild reaction conditions at palladium loads as low as 500 ppm.