Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.
An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired beta-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp(3))-C(sp(2)) bond formation.
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Chong
C
Han
Stephen L
SL
Buchwald
D001555:Benzene Derivatives / Q000138:chemical synthesis*; D001969:Bromobenzenes / Q000737:chemistry*; D002384:Catalysis; D002722:Chlorobenzenes / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D015032:Zinc / Q000737:chemistry*
D001555:Benzene Derivatives; D001969:Bromobenzenes; D002722:Chlorobenzenes; D009942:Organometallic Compounds; D010165:Palladium; D015032:Zinc