Efficient synthesis of sterically crowded biaryls by palladium-phosphinous acid-catalyzed cross-coupling of aryl halides and aryl grignards.
A series of sterically hindered biaryls have been obtained by palladium- and nickel-phosphinous acid-catalyzed Kumada-Corriu cross-coupling of ortho-substituted aryl halides and Grignard reagents. This method allows formation of di- and tri-ortho-substituted biaryls in 87-98% yield under mild reaction conditions even when electron-rich aryl chlorides are used. The reaction also proceeds with aryl iodides at -20 degrees C, and under these conditions, functional groups that are generally not compatible with Grignard reagents are tolerated.
Department of Chemistry, Georgetown University, Washington, DC 20057, USA. cw27@georgetown.edu
Christian
C
Wolf
Hanhui
H
Xu
D001713:Biphenyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D008024:Ligands; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D017976:Phosphorus Acids / Q000737:chemistry*; D013237:Stereoisomerism
D001713:Biphenyl Compounds; D006846:Hydrocarbons, Halogenated; D008024:Ligands; D009942:Organometallic Compounds; D017976:Phosphorus Acids; D010165:Palladium