Ylide‐Functionalized Diisopropyl Phosphine (prYPhos): A Ligand for Selective Suzuki‐Miyaura Couplings of Aryl Chlorides
Xiao‐Jing Wei, Bingxiang Xue, Jens Handelmann, Zhiyong Hu, Heidar Darmandeh, Viktoria H. Gessner, Lukas J. Gooßen
Abstract
Abstract The ylide‐functionalized diisopropyl phosphine (prYPhos) promotes Pd‐catalyzed Suzuki‐Miyaura couplings of aryl chlorides and bromides with arylboronic acids. Using Pd 2 (dba) 3 /prYPhos as the catalyst and K 2 CO 3 as the base, various (hetero)biaryls were synthesized in 45–98% yields at mild reaction conditions, tolerating sensitive functional groups and steric hindrance. The electron rich, sterically demanding ligand induces a high selectivity for halides versus triflate. Chloroaryl triflates were selectively coupled at the chloride, leaving inherently more reactive triflate groups in place. magnified image
Topics & Concepts
ChemistrySteric effectsTrifluoromethanesulfonateArylPhosphineYlideLigand (biochemistry)Aryl halideCatalysisHalideMedicinal chemistryChlorideOrganic chemistryCombinatorial chemistryPolymer chemistryAlkylBiochemistryReceptorCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry