944042-22-2Relevant academic research and scientific papers
Nickel-catalyzed cross-coupling of phenols and arylboronic acids through an in situ phenol activation mediated by PyBroP
Chen, Guo-Jun,Huang, Jie,Gao, Lian-Xun,Han, Fu-She
, p. 4038 - 4042 (2011)
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 [NiCl2(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 NH2 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.
Aryl phosphoramides: useful electrophiles for suzuki-miyaura coupling catalyzed by a NiCl2/dppp system (dppp=1,3-bis(diphenylphosphino) propane)
Zhao, Yu-Long,Li, You,Li, Yu,Gao, Lian-Xun,Han, Fu-She
supporting information; experimental part, p. 4991 - 4994 (2010/08/05)
Chemical Equation presantation Suzuki-Miyaura coupling: We disclose a new strategy for phenol activation in the first Suzuki-Miyaura coupling of phenol derivatives activated by forming aryl bis(2-oxo-3-oxazolidinyl)phosphines as a highly efficient and broadly applicable methodology for the diverse synthesis of biaryls and heterobiaryls (see scheme). The use of readily available, stable NiCl2/dppp as the catalyst system also provides an important advance.
