Rapid and efficient microwave-assisted amination of electron-rich aryl halides without a transition-metal catalyst.
作者： Lei Shi , Min Wang , Chun-An Fan , Fu-Min Zhang , Yong-Qiang Tu
DOI: 10.1021/OL0353868
关键词: Electron 、 Regioselectivity 、 Aryl 、 Amination 、 Aryne 、 Halide 、 Catalysis 、 Transition metal 、 Chemistry 、 Photochemistry
摘要: [reaction: see text] A rapid and direct amination of aryl halides has been developed in good to high yields under microwave irradiation without a transition-metal catalyst. This reaction is particularly powerful method for the coupling electron-rich with various amines. In some cases, excellent regioselectivity could be observed, which facilitated preparation meta-substituted anilines from ortho- or para-substituted phenylhalides. addition, mechanism via interesting benzyne intermediate proposed.
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sci-hub.se 参考文章(13)
Artis Klapars, Xiaohua Huang, Stephen L. Buchwald, A general and efficient copper catalyst for the amidation of aryl halides. Journal of the American Chemical Society. ,vol. 124, pp. 7421- 7428 ,(2002) , 10.1021/JA0260465
Giuseppe D'Aprano, Mario Leclerc, Gianni Zotti, Gilberto Schiavon, Synthesis and Characterization of Polyaniline Derivatives: Poly(2-alkoxyanilines) and Poly(2,5-dialkoxyanilines) Chemistry of Materials. ,vol. 7, pp. 33- 42 ,(1995) , 10.1021/CM00049A008
Artis Klapars, Jon C. Antilla, Xiaohua Huang, Stephen L. Buchwald, A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles Journal of the American Chemical Society. ,vol. 123, pp. 7727- 7729 ,(2001) , 10.1021/JA016226Z
Joseph F. Bunnett, Roland E. Zahler, Aromatic Nucleophilic Substitution Reactions. Chemical Reviews. ,vol. 49, pp. 273- 412 ,(1951) , 10.1021/CR60153A002
H. Heaney, The Benzyne and Related Intermediates. Chemical Reviews. ,vol. 62, pp. 81- 97 ,(1962) , 10.1021/CR60216A001
Mats Larhed, Christina Moberg, Anders Hallberg, Microwave-accelerated homogeneous catalysis in organic chemistry. Accounts of Chemical Research. ,vol. 35, pp. 717- 727 ,(2002) , 10.1021/AR010074V
O. L. Chapman, K. Mattes, C. L. McIntosh, J. Pacansky, G. V. Calder, G. Orr, Photochemical transformations. LII. Benzyne Journal of the American Chemical Society. ,vol. 95, pp. 6134- 6135 ,(1973) , 10.1021/JA00799A060
Barry B. Snider, Feng He, Bruce M. Foxman, Total Syntheses of (−)-Asperlicin and (−)-Asperlicin C Journal of the American Chemical Society. ,vol. 120, pp. 6417- 6418 ,(1998) , 10.1021/JA9809408
Iram Goldberg, Ueber Phenylirungen bei Gegenwart von Kupfer als Katalysator European Journal of Inorganic Chemistry. ,vol. 39, pp. 1691- 1692 ,(1906) , 10.1002/CBER.19060390298
John F. Hartwig, Transition Metal Catalyzed Synthesis of Arylamines and Aryl Ethers from Aryl Halides and Triflates: Scope and Mechanism Angewandte Chemie International Edition. ,vol. 37, pp. 2046- 2067 ,(1998) , 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO;2-L