Sequential Ni-catalyzed borylation and cross-coupling of aryl halides via in situ prepared neopentylglycolborane.
A procedure for NiCl(2)(dppp)-catalyzed pinacolborylation and neopentylglycolborylation that utilizes in situ prepared inexpensive pinacolborane and neopentylglycolborane is reported. The scope of this reaction was demonstrated with a variety of aryl bromides and iodides. The resulting aryl neopentylglycolboronic esters undergo a NiCl(2)(dppe)-catalyzed cross-coupling with aryl halides, resulting in an extremely efficient and cost-effective method for the synthesis of functional biaryls, dendritic building blocks, and other complex architectures.
Rosen
Brad M
BM
Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104-6323, USA.
Huang
Chenghong
C
Percec
Virgil
V
D001713:Biphenyl Compounds / Q000138:chemical synthesis; D001892:Camphanes / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry*
D001713:Biphenyl Compounds; D001892:Camphanes; D006846:Hydrocarbons, Halogenated; D009532:Nickel