Studies on the Mechanism of the Transition Metal-Catalyzed Reaction of Organonitrile with Sodium Azide
- Corresponding author: Huang Rongyi, aqhuangry@hotmail.com Xu Heng, aqxuhengg@163.com
Citation: Huang Rongyi, Shen Qiong, Zhang Chao, Zhang Shaoyong, Xu Heng. Studies on the Mechanism of the Transition Metal-Catalyzed Reaction of Organonitrile with Sodium Azide[J]. Acta Chimica Sinica, ;2020, 78(6): 565-571. doi: 10.6023/A20030084
Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2110.
doi: 10.1002/1521-3773(20020617)41:12<2110::AID-ANIE2110>3.0.CO;2-7
Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2113.
doi: 10.1002/1521-3773(20020617)41:12<2113::AID-ANIE2113>3.0.CO;2-Q
Wu, T.; Yi, B. H.; Li, D. Inorg. Chem. 2005, 44, 4130.
doi: 10.1021/ic050063o
Ye, Q.; Wang, X. S.; Zhao, H.; Xiong, R. G. Chem. Soc. Rew. 2005, 34, 208.
doi: 10.1039/B407253G
Chen, X. M.; Tong, M. L. Acc. Chem. Res. 2007, 40, 162.
doi: 10.1021/ar068084p
Li, J. R.; Tao, Y.; Yu, Q.; Bu, X. H. Chem. Commun. 2007, 1527.
Zhao, H.; Qu, Z. R.; Ye, H. Y.; Xiong, R. G. Chem. Soc. Rev. 2008, 37, 84.
doi: 10.1039/B616738C
Shang, J.; Zhang, J.; Cui, Y.; Zhang, T.; Shu, Y.; Yang, L. Acta Chim. Sinica 2010, 68, 233 (in Chinese).
Cantillo, D.; Gutmann, B.; Oliver Kappe, C. J. Am. Chem. Soc. 2011, 133, 4465.
doi: 10.1021/ja109700b
Wang, S. H.; Zheng, F. K.; Wu, M. F.; Liu, Z. F.; Chen, J.; Guo, G. C.; Wu, A. Q. CrystEngComm 2013, 15, 2616.
doi: 10.1039/c3ce27048c
Li, X.; Cheng, L.; Fang, W.; Yang, G. Acta Chim. Sinica 2013, 71, 179 (in Chinese).
Feng, Y.; Liu, X.; Duan, L.; Yang, Q.; Wei, Q.; Xie, G.; Chen, S.; Yang, X.; Gao, S. Dalton Trans. 2015, 44, 2333.
doi: 10.1039/C4DT03131H
Liu, X.; Gao, W.; Sun, P.; Su, Z.; Chen, S.; Wei, Q.; Xie, G.; Gao, S. Green Chem. 2015, 17, 831.
doi: 10.1039/C4GC02184C
Xiong, R. G.; Xue, X.; Zhao, H.; You, X. Z.; Abrahams, B. F.; Xue, Z. Angew. Chem., Int. Ed. 2002, 41, 3800.
doi: 10.1002/1521-3773(20021018)41:20<3800::AID-ANIE3800>3.0.CO;2-3
Jin, T.; Kitahara, F. K.; Kamijo, S.; Yamamoto, Y. Chem. Asian J. 2008, 3, 1575.
doi: 10.1002/asia.200800085
Himo, F.; Demko, Z. P.; Noodleman, L.; Sharpless, K. B. J. Am. Chem. Soc. 2003, 125, 9983.
doi: 10.1021/ja030204q
Zhong, D. C.; Wen, Y. Q.; Deng, J. H.; Luo, X. Z.; Gong, Y. N.; Lu, T. B. Angew. Chem., Int. Ed. 2015, 54, 11795.
doi: 10.1002/anie.201505118
Cantillo, D.; Gutmann, B.; Kappe, C. O. J. Am. Chem. Soc. 2011, 133, 4465.
doi: 10.1021/ja109700b
Huang, R. Y.; Zhang, C.; Yan, D.; Xiong, Z.; Xu, H.; Ren, X. M. RSC Adv. 2018, 8, 39929.
doi: 10.1039/C8RA08486F
Crèmer, D.; Kraka, E. Croat. Chem. Acta 1984, 57, 1259.
Cremer, D.; Kraka, E. Angew. Chem., Int. Ed. 1984, 23, 67.
doi: 10.1002/anie.198400671
Espinosa, E.; Alkorta, I.; Elguero, J.; Molins, E. J. Chem. Phys. 2004, 387, 481.
Ritter, J. J.; Minieri, P. P. J. Am. Chem. Soc. 1948, 70, 4045.
doi: 10.1021/ja01192a022
Ritter, J. J.; Kalish, J. J. Am. Chem. Soc. 1948, 70, 4048.
doi: 10.1021/ja01192a023
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H.P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT, 2013.
Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
doi: 10.1103/PhysRevB.37.785
Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
doi: 10.1063/1.464913
Andrae, D.; Häuerman, U.; Dolg, M.; Stoll, H.; Preu, H. Theor. Chim. Acta 1990, 77, 123.
doi: 10.1007/BF01114537
Bader, R. F. W. Atoms in Molecules, A Quantum Theory, Oxford University Press, Oxford, 1990.
Boys, S. F.; Bernardi, F. Mol. Phys. 1970, 19, 553.
doi: 10.1080/00268977000101561
Lu, T.; Chen, F. W. J. Comp. Chem. 2012, 33, 580.
doi: 10.1002/jcc.22885
Yingchun ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078
Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo2O4/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
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