A practical ligand-free copper(I) bromide-catalyzed fluoroalkoxylation of unactivated aryl bromides
作者： Ying Guo , Yu-Dao Li , Cheng Chen , Jian-Hong Zhao , Hong-Wei Liu
DOI: 10.1007/S11164-015-2165-4
关键词: Catalysis 、 Aryl 、 Reagent 、 Chemistry 、 Copper(I) bromide 、 Ligand 、 Organic chemistry 、 Nucleophile 、 Formamide 、 Bromide
摘要: An efficient ligand-free fluoroalkoxylation of unactivated aryl bromides has been developed, with special attention focused on practicability the reaction. Without precious metal and organic ligand, reaction was carried out under catalytic system inexpensive copper(I) bromide as a catalyst, N,N-dimethyl formamide cocatalyst, corresponding stoichiometric sodium fluoroalkoxide nucleophilic reagent. The facile approach avoids drawbacks associated cost, separation pollution ligand to enable sustainable access fluoroalkyl ethers from readily available bromoarenes.
springer.com
sci-hub.se 参考文章(27)
Imma Güell, Xavi Ribas, Ligand-Free Ullmann-Type C–Heteroatom Couplings Under Practical Conditions European Journal of Organic Chemistry. ,vol. 2014, pp. 3188- 3195 ,(2014) , 10.1002/EJOC.201400033
Frédéric Leroux, Peter Jeschke, Manfred Schlosser, α-Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species Chemical Reviews. ,vol. 105, pp. 827- 856 ,(2005) , 10.1021/CR040075B
Valentina Dichiarante, Andrea Salvaneschi, Stefano Protti, Daniele Dondi, Maurizio Fagnoni, Angelo Albini, The β Effect of Silicon in Phenyl Cations Journal of the American Chemical Society. ,vol. 129, pp. 15919- 15926 ,(2007) , 10.1021/JA074778X
Ying Guo, Si-Zhe Ji, Cheng Chen, Hong-Wei Liu, Jian-Hong Zhao, Yu-Lin Zheng, Ya-Fei Ji, A ligand-free, powerful, and practical method for methoxylation of unactivated aryl bromides by use of the CuCl/HCOOMe/MeONa/MeOH system Research on Chemical Intermediates. ,vol. 41, pp. 8651- 8664 ,(2015) , 10.1007/S11164-014-1917-X
Menno A. Keegstra, Theo H.A. Peters, Lambert Brandsma, Copper(I) halide catalysed synthesis of alkyl aryl and alkyl heteroaryl ethers Tetrahedron. ,vol. 48, pp. 3633- 3652 ,(1992) , 10.1016/S0040-4020(01)88501-X
Josep Irurre, Josefina Casas, Angel Messeguer, Resistance of the 2,2,2-trifluoroethoxy aryl moiety to the cytochrome P-450 metabolism in rat liver microsomes Bioorganic & Medicinal Chemistry Letters. ,vol. 3, pp. 179- 182 ,(1993) , 10.1016/S0960-894X(01)80872-6
William K. Hagmann, The Many Roles for Fluorine in Medicinal Chemistry Journal of Medicinal Chemistry. ,vol. 51, pp. 4359- 4369 ,(2008) , 10.1021/JM800219F
Hitomi Suzuki, Toshiyuki Matuoka, Isao Ohtsuka, Atsuhiro Osuka, Copper(I)-assisted synthesis of aryl 2,2,2-trifluoroethyl ethers Synthesis. ,vol. 1985, pp. 499- 500 ,(1985) , 10.1055/S-1985-31246
Bruce E. Smart, Fluorine substituent effects (on bioactivity) Journal of Fluorine Chemistry. ,vol. 109, pp. 3- 11 ,(2001) , 10.1016/S0022-1139(01)00375-X
Xiao-Jun Tang, Qing-Yun Chen, Copper-Mediated Radical Cross-Coupling Reaction of 2,2-Dichloro-1,1,1-trifluoroethane (HCFC-123) with Phenols or Thiophenols Organic Letters. ,vol. 14, pp. 6214- 6217 ,(2012) , 10.1021/OL302962P