title: Nickel-catalyzed cross-coupling of phenols and arylboronic acids through an in situ phenol activation mediated by PyBroP.
abstract: A new method for the Suzuki-Miyaura cross-coupling of phenols and arylboronic acids through in situ phenol activation mediated by PyBroP is presented. The reaction proceeds efficiently by using cost-effective, markedly stable [NiCl(2)(dppp)] (dppp=1,3-bis(diphenylphosphino)propane) as the catalyst in only 5 mol % loading, as well as in the absence of extra ligands. The method exhibits broad applicability and high efficiency towards a wide range of both phenols and boronic acids, including activated, nonactivated, deactivated, and heteroaromatic coupling partners. In addition, various functional groups, such as ether, amino, cyano, ester, and ketone groups, are compatible with this transformation. Notably, arylboronic acids containing an unprotected NH(2) group and 2-heterocyclic boronic acids, which are generally problematic for coupling under conventional conditions, are also viable substrates, although moderate yields were obtained for sterically hindered substrates. Consequently, the in situ cross-coupling methodology coupled with the use of an inexpensive and stable nickel catalyst provides a rapid and efficient pathway for the assembly of biaryls and heterobiaryls with structural diversity from readily available phenol compounds.
authors.affiliation: Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, Jilin, PR China.
authors.forename: Guo-Jun
authors.initials: GJ
authors.lastname: Chen
authors.forename: Jie
authors.initials: J
authors.lastname: Huang
authors.forename: Lian-Xun
authors.initials: LX
authors.lastname: Gao
authors.forename: Fu-She
authors.initials: FS
authors.lastname: Han
mesh_terms: D001897:Boronic Acids; D002384:Catalysis; D003432:Cross-Linking Reagents / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D019800:Phenol / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D001897:Boronic Acids; D003432:Cross-Linking Reagents; D063065:Organophosphonates; D010720:Phosphines; D019800:Phenol; C467590:1,3-bis(diphenylphosphino)propane; D009532:Nickel; D011407:Propane