title: Nickel-catalyzed borylation of halides and pseudohalides with tetrahydroxydiboron [B2(OH)4].
abstract: Arylboronic acids are gaining increased importance as reagents and target structures in a variety of useful applications. Recently, the palladium-catalyzed synthesis of arylboronic acids employing the atom-economical tetrahydroxydiboron (BBA) reagent has been reported. The high cost associated with palladium, combined with several limitations of both palladium- and copper-catalyzed processes, prompted us to develop an alternative method. Thus, the nickel-catalyzed borylation of aryl and heteroaryl halides and pseudohalides using tetrahydroxydiboron (BBA) has been formulated. The reaction proved to be widely functional group tolerant and applicable to a number of heterocyclic systems. To the best of our knowledge, the examples presented here represent the only effective Ni-catalyzed Miyaura borylations conducted at room temperature.
authors.affiliation: Roy and Diana Vagelos Laboratories and Penn/Merck Laboratory for High Throughput Experimentation, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, USA. gmolandr@sas.upenn.edu
authors.forename: Gary A
authors.initials: GA
authors.lastname: Molander
authors.forename: Livia N
authors.initials: LN
authors.lastname: Cavalcanti
authors.forename: Carolina
authors.initials: C
authors.lastname: García-García
mesh_terms: D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D001896:Boron Compounds; D006846:Hydrocarbons, Halogenated; D009942:Organometallic Compounds; D009532:Nickel