Chinese Journal of Organic Chemistry >
Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles
Received date: 2023-08-17
Revised date: 2023-10-19
Online published: 2023-11-08
Supported by
Natural Science Foundation of Hubei Province(2021CFB160)
An efficient synthesis of α-aminonitriles via nucleophilic substitution of α-cyanohydrin methanesulfonates with aromatic amines was developed. This transition metal-free protocol has the advantages of cheap and easily available starting materials, broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Furthermore, this strategy could also be applicable to quaternary α-cyanohydrin methanesulfonates and various nitrogen nucleophiles. A range of derivatives were readily obtained through subsequent elaboration of α-aminonitriles.
Yong Zhang , Zhigao Tian , Lin Huang , Qiufei Hou , Honghong Fan , Wanqiang Wang . Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles[J]. Chinese Journal of Organic Chemistry, 2024 , 44(2) : 561 -572 . DOI: 10.6023/cjoc202308015
| [1] | (a) Feldman, P. L.; Brackeen, M. F. J. Org. Chem. 1990, 55, 4207. |
| [1] | (b) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359. |
| [1] | (c) Connon S. J. Angew. Chem.. Int. Ed. 2008, 47, 1176. |
| [1] | (d) Wang, J.; Liu, X.; Feng, X. Chem. Rev. 2011, 111, 6947. |
| [1] | (d) Zhang, F.-G.; Zhu, X.-Y.; Li, S.; Nie, J.; Ma, J.-A. Chem. Commun. 2012, 48, 11552. |
| [1] | (e) Bachon, A.-K.; Opatz, T. J. Org. Chem. 2016, 81, 1858. |
| [1] | (f) Kurono, N.; Ohkuma, T. ACS Catal. 2016, 6, 989. |
| [1] | (g) Kouznetsov, V. V.; Galvis, C. E. P. Tetrahedro. 2018, 74, 773. |
| [1] | (h) Grundke, C.; Vierengel, N.; Opatz, T. Chem. Rec. 2020, 20, 989. |
| [1] | (i) Ullah, B.; Gupta, N. K.; Ke, Q.; Ullah, N.; Cai, X.; Liu, D. Catalyst. 2022, 12, 1149. |
| [1] | (j) Zhou, Y.; Chen, H.; Lei, P.; Gui, C.; Wang, H.; Yan, Q.; Wang, W.; Chen, F. Chin. Chem. Lett. 2022, 33, 4850. |
| [2] | Fukuyama, T.; Yang, L.; Ajeck, K. L.; Sachleben, R. A. J. Am. Chem. Soc. 1990, 112, 3712. |
| [3] | Martinez, E. J.; Owa, T.; Schreiber, S. L.; Corey, E. J. Proc. Natl. Acad. Sci. U. S. A. 1999, 96, 3496. |
| [4] | Carre?o Otero, A. L.; Vargas Méndez, L. Y.; Duque L, J. E.; Kouznetsov, V. V. Eur. J. Med. Chem. 2014, 78, 392. |
| [5] | Gauthier, J. Y.; Chauret, N.; Cromlish, W.; Desmarais, S.; Duong, L. T.; Falgueyret, J.-P.; Kimmel, D. B.; Lamontagne, S.; Léger, S.; LeRiche, T.; Li, C. S.; Massé, F.; McKay, D. J.; Nicoll-Griffith, D. A.; Oballa, R. M.; Palmer, J. T.; Percival, M. D.; Riendeau, D.; Robichaud, J.; Rodan, G. A.; Rodan, S. B.; Seto, C.; Thérien, M.; Truong, V.-L.; Venuti, M. C.; Wesolowski, G.; Young, R. N.; Zamboni, R.; Black, W. C. Bioorg. Med. Chem. Lett. 2008, 18, 923. |
| [6] | Deacon, C. F.; Holst, J. J. Adv. Thermoelectr. 2009, 26, 488. |
| [7] | Kuhn, B.; Hennig, M.; Mattei, P. Curr. Top. Med. Chem. 2007, 7, 609. |
| [8] | Strecker A. Liebigs Ann. Chem. 1850, 75, 27. |
| [9] | (a) Shen, K.; Liu, X.; Cai, Y.; Lin, L.; Feng, X. Chem.-Eur. J. 2009, 15, 6008. |
| [9] | (b) Harusawa, S.; Shioiri, T. Tetrahedro. 2016, 72, 8125. |
| [9] | (c) Ishitani, H.; Komiyama, S.; Hasegawa, Y.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 762. |
| [9] | (d) Davis, F. A.; Reddy, R. E.; Portonovo, P. S. Tetrahedron Lett. 1994, 35, 9351. |
| [9] | (e) Cruz-Acosta, F.; Santos-Expósito, A.; de Armas, P.; García-Tellado, F. Chem. Commun. 2009, 6839. |
| [9] | (f) Abell, J. P.; Yamamoto, H. J. Am. Chem. Soc. 2009, 131, 15118. |
| [10] | (a) Sun, P.; Qian, C.; Wang, L.; Chen, R. Synth. Commun. 2002, 32, 2973. |
| [10] | (b) Ranu, B. C.; Dey, S. S.; Hajra, A. Tetrahedro. 2002, 58, 2529. |
| [10] | (c) De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2004, 45, 7407. |
| [10] | (d) De S. K. J. Mol. Catal. A: Chem. 2005, 225, 169. |
| [10] | (e) De S. K. Synth. Commun. 2005, 35, 653. |
| [10] | (f) Paraskar, A. S.; Sudalai, A. Tetrahedron Lett. 2006, 47, 5759. |
| [11] | Pan, S. C.; List, B. Synlet. 2007, 2007, 0318. |
| [12] | Das, B.; Ramu, R.; Ravikanth, B.; Reddy, K. R. Synthesi. 2006, 2006, 1419. |
| [13] | Royer, L.; De, S. K.; Gibbs, R. A. Tetrahedron Lett. 2005, 46, 4595. |
| [14] | (a) Zhang, Y.; Peng, H.; Zhang, M.; Cheng, Y.; Zhu, C. Chem. Commun. 2011, 47, 2354. |
| [14] | (b) Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317. |
| [14] | (c) Sonobe, T.; Oisaki, K.; Kanai, M. Chem. Sci. 2012, 3, 3249. |
| [14] | (d) Tanoue, A.; Yoo, W.-J.; Kobayashi, S. Org. Lett. 2014, 16, 2346. |
| [14] | (e) Ushakov, D. B.; Gilmore, K.; Kopetzki, D.; McQuade, D. T.; Seeberger, P. H. Angew. Chem.. Int. Ed. 2014, 53, 557. |
| [14] | (f) Wagner, A.; Ofial, A. R. J. Org. Chem. 2015, 80, 2848. |
| [14] | (g) Shen, H.; Hu, L.; Liu, Q.; Hussain, M. I.; Pan, J.; Huang, M.; Xiong, Y. Chem. Commun. 2016, 52, 2776. |
| [14] | (h) Vega, J. A.; Alonso, J. M.; Méndez, G.; Ciordia, M.; Delgado, F.; Trabanco, A. A. Org. Lett. 2017, 19, 938. |
| [14] | (i) Patil, M. R.; Dedhia, N. P.; Kapdi, A. R.; Kumar, A. V. J. Org. Chem. 2018, 83, 4477. |
| [14] | (j) Nauth, A. M.; Schechtel, E.; D?ren, R.; Tremel, W.; Opatz, T. J. Am. Chem. Soc. 2018, 140, 14169. |
| [14] | (k) Wakaki, T.; Sakai, K.; Enomoto, T.; Kondo, M.; Masaoka, S.; Oisaki, K.; Kanai, M. Chem.-Eur. J. 2018, 24, 8051. |
| [14] | (l) Mudithanapelli, C.; Dhorma, L. P.; Kim, M.-H. Org. Lett. 2019, 21, 3098. |
| [14] | (m) Shi, S.; Yang, X.; Tang, M.; Hu, J.; Loh, T.-P. Org. Lett. 2021, 23, 4018. |
| [15] | (a) Shirokane, K.; Kurosaki, Y.; Sato, T.; Chida, N. Angew. Chem.. Int. Ed. 2010, 49, 6369. |
| [15] | (b) Inamoto, Y.; Kaga, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Org. Lett. 2013, 15, 3452. |
| [15] | (c) Nakajima, M.; Sato, T.; Chida, N. Org. Lett. 2015, 17, 1696. |
| [15] | (d) Fuentes de Arriba, á. L.; Lenci, E.; Sonawane, M.; Formery, O.; Dixon, D. J. Angew. Chem.. Int. Ed. 2017, 56, 3655. |
| [15] | (e) Trillo, P.; Slagbrand, T.; Adolfsson, H. Angew. Chem.. Int. Ed. 2018, 57, 12347. |
| [15] | (f) Ong, D. Y.; Fan, D.; Dixon, D. J.; Chiba, S. Angew. Chem.. Int. Ed. 2020, 59, 11903. |
| [15] | (g) Yan, F.; Huang, Z.; Du, C.-X.; Bai, J.-F.; Li, Y. J. Catal. 2021, 395, 188. |
| [15] | (h) Yu, B.; Bodinier, F.; Saague-Tenefo, M.; Gerardo, P.; Ardisson, J.; Lannou, M.-I.; Sorin, G. Eur. J. Org. Chem. 2021, 2021, 3634. |
| [15] | (i) Liu, L.; Liu, Y.; Shen, X.; Zhang, X.; Deng, S.; Chen, Y. J. Org. Chem. 2022, 87, 6321. |
| [16] | Liu, T.-L.; Li, Z.-F.; Tao, J.; Li, Q.-H.; Li, W.-F.; Li, Q.; Ren, L.-Q.; Peng, Y.-G. Chem. Commun. 2020, 56, 651. |
| [17] | (a) Wang, L.-G.; Zheng, Y.-X.; Zhou, X.; Wang, H.-F.; Yan, Q.-J.; Wang, W.; Chen, F.-E. Chin. J. Org. Chem. 2023, 43, 668 (in Chinese). |
| [17] | (王雷刚, 郑逸轩, 周希, 王海峰, 严琼姣, 汪伟, 陈芬儿, 有机化学. 2023, 43, 668.) |
| [17] | (b) Liu, S.; Meng, L.; Zeng, X.; Hammond, G. B.; Xu, B. Chin. J. Chem. 2021, 39, 913. |
| [18] | (a) Ueda, M.; Nishimura, K.; Ryu, I. Synlet. 2013, 24, 1683. |
| [18] | (b) Wu, G.; Xu, S.; Deng, Y.; Wu, C.; Zhao, X.; Ji, W.; Zhang, Y.; Wang, J. Tetrahedro. 2016, 72, 8022. |
| [18] | (c) Li, C.; Zhang, Y.; Sun, Q.; Gu, T.; Peng, H.; Tang, W. J. Am. Chem. Soc. 2016, 138, 10774. |
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