Palladium-Catalyzed sp3 C–H Nitration of 8-Methylquinolines
作者： Wei Zhang , Shaobo Ren , Jian Zhang , Yunkui Liu
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摘要: Palladium-catalyzed nitration of 8-methylquinolines with t-BuONO to give 8-(nitromethyl)quinolines in moderate excellent yields has been developed involving an sp3 C–H bond activation. The resulting (nitromethyl)quinolines could be selectively reduced (1,2,3,4-tetrahydroquinolin-8-yl)methanamines by NaBH4 the presence a catalytic amount NiCl2·6H2O.
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sci-hub.se 参考文章(43)
G. K. Surya Prakash, Thomas Mathew, ipso-Nitration of arenes. Angewandte Chemie. ,vol. 49, pp. 1726- 1728 ,(2010) , 10.1002/ANIE.200906940
Alessandro Palmieri, Serena Gabrielli, Roberto Ballini, Efficient two-step sequence for the synthesis of 2,5-disubstituted furan derivatives from functionalized nitroalkanes: successive Amberlyst A21- and Amberlyst 15-catalyzed processes Chemical Communications. ,vol. 46, pp. 6165- 6167 ,(2010) , 10.1039/C0CC01097A
G. K. Surya Prakash, Chiradeep Panja, Thomas Mathew, Vijayalakshmi Surampudi, Nicos A. Petasis, George A. Olah, ipso-Nitration of Arylboronic Acids with Chlorotrimethylsilane−Nitrate Salts Organic Letters. ,vol. 6, pp. 2205- 2207 ,(2004) , 10.1021/OL0493249
George A. Olah, Henry C. H. Lin, Electrophilic reactions at single bonds. V. Nitration and nitrolysis of alkanes and cycloalkanes with nitronium salts Journal of the American Chemical Society. ,vol. 93, pp. 1259- 1261 ,(1971) , 10.1021/JA00734A039
Wei Zhang, Jian Zhang, Shaobo Ren, Yunkui Liu, Palladium-Catalyzed Aromatic C–H Bond Nitration Using Removable Directing Groups: Regiospecific Synthesis of Substituted o-Nitrophenols from Related Phenols Journal of Organic Chemistry. ,vol. 79, pp. 11508- 11516 ,(2014) , 10.1021/JO502145V
Srimanta Manna, Sandipan Jana, Tapish Saboo, Arun Maji, Debabrata Maiti, Synthesis of (E)-nitroolefins via decarboxylative nitration using t-butylnitrite (t-BuONO) and TEMPO Chemical Communications. ,vol. 49, pp. 5286- 5288 ,(2013) , 10.1039/C3CC41576G
Shlomo Rozen, Mira Carmeli, From Azides to Nitro Compounds in a Few Seconds Using HOF·CH3CN Journal of the American Chemical Society. ,vol. 125, pp. 8118- 8119 ,(2003) , 10.1021/JA035616D
Keita Tani, Kirill Lukin, Philip E. Eaton, NITRATION OF ORGANOLITHIUMS AND GRIGNARDS WITH DINITROGEN TETROXIDE : SUCCESS AT MELTING INTERFACES Journal of the American Chemical Society. ,vol. 119, pp. 1476- 1477 ,(1997) , 10.1021/JA963658E
Guobing Yan, Minghua Yang, Recent advances in the synthesis of aromatic nitro compounds Organic and Biomolecular Chemistry. ,vol. 11, pp. 2554- 2566 ,(2013) , 10.1039/C3OB27354G
Degui Wu, Jian Zhang, Jianhai Cui, Wei Zhang, Yunkui Liu, AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C–H bond and direct conversion of 2-methyl quinoxalines into related nitriles Chemical Communications. ,vol. 50, pp. 10857- 10860 ,(2014) , 10.1039/C4CC01327A