A site-selective and stereospecific cascade Suzuki–Miyaura annulation of alkyl 1,2-bisboronic esters and 2,2′-dihalo 1,1′-biaryls
Suzanne Willems, Georgios Toupalas, Julia C. Reisenbauer, Bill Morandi
Abstract
A cascade Suzuki-Miyaura cross-coupling giving rise to 9,10-dihydrophenanthrenes has been developed. Using biaryls with unsymmetrical substitution-pattern full site-selectivity was observed. Furthermore, this cross-coupling of an alkyl 1,2-bisboronic pinacol ester proceeds through the challenging coupling of a secondary boronate with complete stereoretention.
Topics & Concepts
CascadeChemistryAlkylStereospecificityAnnulationCoupling (piping)SelectivityCombinatorial chemistryStereochemistryBase (topology)Organic chemistryCatalysisMaterials scienceMathematicsMathematical analysisChromatographyMetallurgyCatalytic Cross-Coupling ReactionsChemical synthesis and alkaloidsSynthetic Organic Chemistry Methods