An improved protocol for synthesis of N-arylamides and benzoxazoles by the copper-catalyzed reaction of aryl halides with nitriles
作者： Dong-Xue Zhang , Shi-Kai Xiang , Hao Hu , Wen Tan , Chun Feng
DOI: 10.1016/J.TET.2013.09.059
关键词: Organic chemistry 、 Benzoxazole 、 Hydrolysis 、 Aryl 、 Acetaldoxime 、 Weak base 、 Halide 、 Copper catalyzed 、 Reagent 、 Chemistry
摘要: Abstract An improved protocol for the synthesis of N-arylamides and benzoxazoles by copper-catalyzed reaction aryl halides with nitriles has been developed. Use acetaldoxime as hydrolysis reagent instead H2O facilitates operation reaction. The significantly decreased amount nitriles, along use weak base K2CO3 strong KOH, makes this transformation atom-efficient environmentally benign. A variety benzoxazole derivatives can be synthesized according to approach.
elsevier.com
sci-hub.se 参考文章(37)
Dan-Wei Zhang, Xin Zhao, Jun-Li Hou, Zhan-Ting Li, Aromatic Amide Foldamers: Structures, Properties, and Functions Chemical Reviews. ,vol. 112, pp. 5271- 5316 ,(2012) , 10.1021/CR300116K
David S. Surry, Stephen L. Buchwald, Diamine ligands in copper -catalyzed reactions Chemical Science. ,vol. 1, pp. 13- 31 ,(2010) , 10.1039/C0SC00107D
Zhengkai Li, Lixia Wang, Xiangge Zhou, An Efficient and Practical Protocol for Catalytic Hydrolysis of Nitriles by a Copper(I) Complex in Water Advanced Synthesis & Catalysis. ,vol. 354, pp. 584- 588 ,(2012) , 10.1002/ADSC.201100812
Harold S. Freeman, Jack R. Butler, Leon D. Freedman, Acetyldiarylamines by arylation of acetanilides. Some applications and limitations Journal of Organic Chemistry. ,vol. 10, pp. 4975- 4978 ,(1978) , 10.1021/JO00420A018
Takiya J. Ahmed, Spring Melody M. Knapp, David R. Tyler, Frontiers in catalytic nitrile hydration: Nitrile and cyanohydrin hydration catalyzed by homogeneous organometallic complexes Coordination Chemistry Reviews. ,vol. 255, pp. 949- 974 ,(2011) , 10.1016/J.CCR.2010.08.018
Jos H.M Lange, Lovina J.F Hofmeyer, Floris A.S Hout, Stefan J.M Osnabrug, Peter C Verveer, Chris G Kruse, Rolf W Feenstra, Microwave-enhanced Goldberg reaction: a novel route to N-arylpiperazinones and N-arylpiperazinediones Tetrahedron Letters. ,vol. 43, pp. 1101- 1104 ,(2002) , 10.1016/S0040-4039(01)02334-6
Eun Sun Kim, Hyun Seung Lee, Sung Hwan Kim, Jae Nyoung Kim, An efficient InCl3-catalyzed hydration of nitriles to amides: acetaldoxime as an effective water surrogate Tetrahedron Letters. ,vol. 51, pp. 1589- 1591 ,(2010) , 10.1016/J.TETLET.2010.01.063
Soledad Royo Gracia, Katharina Gaus, Norbert Sewald, Synthesis of chemically modified bioactive peptides: recent advances, challenges and developments for medicinal chemistry Future Medicinal Chemistry. ,vol. 1, pp. 1289- 1310 ,(2009) , 10.4155/FMC.09.97
Dawei Ma, Qian Cai, Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles. Accounts of Chemical Research. ,vol. 41, pp. 1450- 1460 ,(2008) , 10.1021/AR8000298
Eric Valeur, Mark Bradley, Amide Bond Formation: Beyond the Myth of Coupling Reagents Chemical Society Reviews. ,vol. 38, pp. 606- 631 ,(2009) , 10.1039/B701677H