Chinese Journal of Organic Chemistry >
Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions
Received date: 2022-04-13
Revised date: 2022-06-10
Online published: 2022-06-23
Supported by
National Natural Science Foundation of China(22071063)
As a class of small organic molecules containing (NC) functional groups with high activity, isocyanide has been widely employed in organic synthesis, materials science, as well as coordination chemistry. In recent years, the transition metal-catalyzed isocyanide insertion reactions have attracted much attention due to the convenient and simple operations, the efficiency in the formation of diverse new bonds and good reaction selectivity. A series of highly useful chain or cyclic compounds have been successfully constructed using this strategy, such as functionalized ketones, amides, nitrogen heterocyclic compounds, etc. To study the most recent progress, the advances in transition metal-catalyzed isocyanide insertion reactions since 2017 to 2021 are briefly summarized according to different metal categories, and the future development has also been prospected in this review.
Qiushan Gao , Meng Li , Wanqing Wu . Recent Advances in Transition Metal-Catalyzed Isocyanide Insertion Reactions[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2659 -2681 . DOI: 10.6023/cjoc202204007
| [1] | Patil, P.; Ahmadian-Moghaddam, M.; Dömling, A. Green Chem. 2020, 22, 6902. |
| [2] | Ramozzi, R.; Chéron, N.; Braïda, B.; Hiberty, P. C.; Fleurat-Lessard, P. New J. Chem. 2012, 36, 1137. |
| [3] | Saegusa, T.; Ito, Y.; Kobayashi, S.; Hirota, K.; Yoshioka, H. Tetrahedron Lett. 1966, 6121. |
| [4] | (a) Saluste, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Int. Ed. 2000, 39, 4156. |
| [4] | (b) Saluste, C. G.; Whitby, R. J.; Furber, M. Tetrahedron Lett. 2001, 42, 6191. |
| [4] | (c) Whitby, R. J.; Saluste, C. J.; Furber, M. Org. Biomol. Chem. 2004, 2, 1974. |
| [4] | (d) Tetala, K. K. R.; Whitby, R. J.; Light, M. E.; Hursthouse, M. B. Tetrahedron Lett. 2004, 45, 6991. |
| [5] | (a) Vlaar, T.; Cioc, R. C.; Mampuys, P.; Maes, B. U.; Orru, R. V.; Ruijter, E. Angew. Chem., Int. Ed. 2012, 51, 13058. |
| [5] | (b) Vlaar1, T.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. Chem. Heterocycl. Comp. 2013, 49, 902. |
| [6] | (a) Jiang, H.; Liu, B.; Li, Y.; Wang, A.; Huang, H. Org. Lett. 2011, 13, 1028. |
| [6] | (b) Li, Y.; Zhao, J.; Chen, H.; Liu, B.; Jiang, H. Chem. Commun. 2012, 48, 3545. |
| [6] | (c) Liu, B.; Li, Y.; Yin, M.; Wu, W.; Jiang, H. Chem. Commun. 2012, 48, 11446. |
| [6] | (d) Liu, B.; Gao, H.; Yu, Y.; Wu, W.; Jiang, H. J. Org. Chem. 2013, 78, 10319. |
| [6] | (e) Jiang, H.; Yin, M.; Wu, W. Chem. Commun. 2014, 50, 2037. |
| [6] | (f) Jiang, H.; Gao, H.; Liu, B.; Wu, W. Chem. Commun. 2014, 50, 15348. |
| [7] | (a) Wang, Y.; Wang, H.; Peng, J.; Zhu, Q. Org. Lett. 2011, 13, 4604. |
| [7] | (b) Hu, Z.; Liang, D.; Zhao, J.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 7371. |
| [7] | (c) Peng, J.; Liu, L.; Hu, Z.; Huang, J.; Zhu, Q. Chem. Commun. 2012, 48, 3772. |
| [7] | (d) Peng, J.; Zhao, J.; Hu, Z.; Liang, D.; Huang, J.; Zhu, Q. Org. Lett. 2012, 14, 4966. |
| [7] | (e) Wang, J.; Tang, S.; Zhu, Q. Org. Lett. 2016, 18, 3074. |
| [8] | (a) Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257. |
| [8] | (b) Vllar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., nt. Ed. 2013, 52, 7084. |
| [8] | (c) Lang, S. Chem. Soc. Rev. 2013, 42, 4867. |
| [8] | (d) Wang, Y.; Kumar, R. K.; Bi, X. Tetrahedron Lett. 2016, 57, 5730. |
| [8] | (e) Chakrabarty, S.; Choudhary, S.; Doshi, A.; Liu, F. Q.; Mohan, R.; Ravindra, M. P.; Shah, D.; Yang, X.; Fleming, F. F. Adv. Synth. Catal. 2014, 356, 2135. |
| [8] | (f) Boyarskiy, V. P.; Bokach, N. A.; Luzyanin, K. V.; Kukushkin, V. Y. Chem. Rev. 2015, 115, 2698. |
| [8] | (g) Varadi, A.; Palmer, T. C.; Notis Dardashti, R.; Majumdar, S. Molecules 2015, 21, 19. |
| [8] | (h) Wang, H.; Xu, B. Chin. J. Org. Chem. 2015, 35, 588. (in Chinese) |
| [8] | (王浩, 许斌, 有机化学, 2015, 35, 588.) |
| [8] | (i) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. |
| [8] | (j) Wang, Y.; Kumar, R. K.; Bi, X. Tetrahedron Lett. 2016, 57, 5730. |
| [8] | (k) Kaur, T.; Wadhwa, P.; Bagchi, S.; Sharma, A. Chem. Commun. 2016, 52, 6958. |
| [8] | (l) Sadjadi, S.; Heravi, M. M.; Nazari, N. RSC Adv. 2016, 6, 53203. |
| [8] | (m) Giustiniano, M.; Basso, A.; Mercalli, V.; Massarotti, A.; Novellino, E.; Tron, G. C.; Zhu, J. Chem. Soc. Rev. 2017, 46, 1295. |
| [8] | (n) Song, B.; Xu, B. Chem. Soc. Rev. 2017, 46, 1103. |
| [8] | (o) Gomes, G. D. P.; Loginova, Y.; Vatsadze, S. Z.; Alabugin, I. V. J. Am. Chem. Soc. 2018, 140, 14272. |
| [8] | (p) Gu, Z.-Y.; Ji, S.-J. Acta Chim. Sinica 2018, 76, 347. (in Chinese) |
| [8] | (顾正洋, 纪顺俊, 化学学报, 2018, 76, 347.) |
| [8] | (q) Mathiyazhagan, A. D.; Anilkumar, G. Org. Biomol. Chem. 2019, 17, 6735. |
| [8] | (r) Collet, J. W.; Roose, T. B.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., nt. Ed. 2020, 58, 2. |
| [8] | (s) Wang, J.; Li, D.; Li, J.; Zhu, Q. Org. Biomol. Chem. 2021, 19, 6730. |
| [8] | (t) Wang, W.; Liu, T.; Ding, C.-H.; Xu, B. Org. Chem. Front. 2021, 8, 3525. |
| [8] | (u) Zhang, Z.; Tan, P.; Chang, W.; Zhang, Z. Adv. Syn. Catal. 2021, 363, 5344. |
| [9] | Kosugi, M.; Ogata, T.; Tamura, H.; Hiroshi, S.; Toshihiko, M. Chem. Lett. 1986, 15, 1197. |
| [10] | Peng, J.; Gao, Yang.; Zhu, C.; Liu, B.; Gao, Y.; Hu, M.; Wu, W.; Jiang, H. J. Org. Chem. 2017, 82, 3581. |
| [11] | Salehi, P.; Shiri, M. Adv. Synth. Catal. 2018, 361, 118. |
| [12] | Dechert-Schmitt, A.-M.; Garnsey, M. R.; Wisniewska, H. M.; Murray, J. I.; Lee, T.; Kung, D. W.; Sach, N.; Blackmond, D. G. ACS Catal. 2019, 9, 4508. |
| [13] | Chen, B.; Wu, X.-F. Org. Lett. 2020, 22, 636. |
| [14] | Wang, B.; He, D.; Ren, B.; Yao, T. Chem. Commun. 2020, 56, 900. |
| [15] | Yao, T.; Wang, B.; Ren, B.; Qin, X.; Li, T. Chem. Commun. 2021, 57, 4247. |
| [16] | (a) Mampuys, P.; Neumann, H.; Sergeyev, S.; Orru, R. V. A.; Jiao, H.; Spannenberg, A.; Maes, B. U. W.; Beller, M. ACS Catal. 2017, 7, 5549. |
| [16] | (b) Xu, P.; Wang, F.; Wei, T. Q.; Yin, L.; Wang, S. -Y.; Ji, S.-J. Org Lett. 2017, 19, 4484. |
| [16] | (c) Zhang, W.-Z.; Li, H.; Zeng, Y.; Tao, X.; Lu, X. Chin. J. Chem. 2018, 36, 112. |
| [17] | Wang, X.; Xiong, W.; Huang, Y.; Zhu, J.; Hu, Q.; Wu, W.; Jiang, H. Org. Lett. 2017, 19, 5818 |
| [18] | Shiri, M.; Ranjbar, M.; Yasaei, Z.; Zamanian, F.; Notash, B. Org. Biomol. Chem. 2017, 15, 10073. |
| [19] | Ren, Z.-L.; He, P.; Lu, W.-T.; Sun, M.; Ding, M.-W. Org. Biomol. Chem. 2018, 16, 6322. |
| [20] | Huang, K.; Liu, J.-B.; Chen, Z.-F.; Wang, Y.-C.; Yadav, S.; Qiu, G. Org. Lett. 2020, 22, 5931. |
| [21] | Zhu, Y.-M.; Fang, Y.; Li, H.; Xu, X. P.; Ji, S.-J. Org. Lett. 2021, 23, 7342. |
| [22] | Tang, S.; Wang, J.; Xiong, Z.; Xie, Z.; Li, D.; Huang, J.; Zhu, Q. Org. Lett. 2017, 19, 5577. |
| [23] | Sun, H.; Tang, S.; Li, D.; Zhou, Y.; Huang, J.; Zhu, Q. Org. Biomol. Chem. 2018, 16, 3893. |
| [24] | Wang, J.; Gao, D.-W.; Huang, J.; Tang, S.; Xiong, Z.; Hu, H.; You, S.-L.; Zhu, Q. ACS Catal. 2017, 7, 3832. |
| [25] | Luo, S.; Xiong, Z.; Lu, Y.; Zhu, Q. Org. Lett. 2018, 20, 1837. |
| [26] | Teng, F.; Yu, T.; Peng, Y.; Hu, W.; Hu, H.; He, Y.; Luo, S.; Zhu, Q. J. Am. Chem. Soc. 2021, 143, 2722. |
| [27] | Wang, J.; Li, L.; Chai, M.; Ding, S.; Li, J.; Shang, Y.; Zhao, H.; Li, D.; Zhu, Q. ACS Catal. 2021, 11, 12367. |
| [28] | Cheng, S.; Luo, Y.; Yu, T.; Li, J.; Gan, C.; Luo, S.; Zhu, Q. ACS Catal. 2021, 12, 837. |
| [29] | Peng, J.; Gao, Y.; Hu, W.; Gao, Y.; Hu, M.; Wu, W.; Ren, Y.; Jiang, H. Org. Lett. 2016, 18, 5924. |
| [30] | Qiu, G.; Wang, Q.; Zhu, J. Org. Lett. 2017, 19, 270. |
| [31] | Hu, W.; Li, M.; Jiang, G.; Wu, W.; Jiang, H. Org. Lett. 2018, 20, 3500. |
| [32] | Vahabi, A. H.; Alizadeh, A.; Khavasi, H. R.; Bazgir, A. Eur. J. Org. Chem. 2017, 2017, 5347. |
| [33] | Otsuka, S.; Nogi, K.; Yorimitsu, H. Angew. Chem., Int. Ed. 2018, 57, 6653. |
| [34] | Higashimae, S.; Kurata, D.; Kawaguchi, S. I.; Kodama, S.; Sonoda, M.; Nomoto, A.; Ogawa, A. J. Org. Chem. 2018, 83, 5267. |
| [35] | Tran, C. C.; Kawaguchi, S. I.; Kobiki, Y.; Matsubara, H.; Tran, D. P.; Kodama, S.; Nomoto, A.; Ogawa, A. J. Org. Chem. 2019, 84, 11741. |
| [36] | Kodama, S.; Yamamoto, Y.; Kobiki, Y.; Matsubara, H.; Tran, C. C.; Kawaguchi, S. I.; Nomoto, A.; Ogawa, A. Materials 2021, 14. |
| [37] | Lu, F.; Chen, Z.; Li, Z.; Wang, X.; Peng, X.; Li, C.; Fang, L.; Liu, D.; Gao, M.; Lei, A. Org. Lett. 2017, 19, 3954. |
| [38] | Chen, Z.-B.; Liu, K.; Zhang, F.-L.; Yuan, Q.; Zhu, Y.-M. Org. Biomol. Chem. 2017, 15, 8078. |
| [39] | (a) Qian, C.; Liu, K.; Tao, S.-W.; Zhang, F.-L.; Zhu Y.-Ming.; Yang, S.-L. J. Org. Chem. 2018, 83, 9201. |
| [39] | (b) Xia, Y.; Yang, Z.-Y.; Hour, M.-J.; Kuo, S.-C.; Xia, P.; Bastow, K. F.; Nakanishi, Y.; Nampoothiri, P.; Hackl, T.; Hamel, E.; Lee, K. H. Bioorg. Med. Chem. Lett. 2001, 11, 1193. |
| [40] | Gao, M.; Zou, M.; Wang, J.; Tan, Q.; Liu, B.; Xu, B. Org. Lett. 2019, 21, 1593. |
| [41] | Xiong, Z.; Liang, D.; Luo, S. Org. Chem. Front. 2017, 4, 1103. |
| [42] | Luo, L.; Chen, X.-P.; Li, Z.-F.; Zhou, Y.; Xiao, Y.-C.; Chen, F.-E. Org. Biomol. Chem. 2021, 19, 4364. |
| [43] | Luo, L.; Xiong, T.; Zhou, L.; Zeng, Q.; Xiao, Y.-C.; Chen, F.-E. Asian J. Org. Chem. 2021, 10, 2927. |
| [44] | Wu, W.; Li, M.; Zheng, J.; Hu, W.; Li, C.; Jiang, H. Chem. Commun. 2018, 54, 6855. |
| [45] | (a) Chen, D.; Shan, Y.; Li, J.; You, J.; Sun, X.; Qiu, G. Org. Lett. 2019, 21, 4044. |
| [45] | (b) Chen, D.; Yang, M.; Li, J.; Cui, P.; Su, L.; Shan, Y.; You, J.; Rojsitthisak, P.; Liu, J. B.; Qiu, G. J. Org. Chem 2020, 85, 6441. |
| [45] | (c) Shan, Y.; Su, L.; Chen, D.; Yang, M.; Xie, W.; Qiu, G. Chin. Chem. Lett. 2021, 32, 437. |
| [46] | Zhu, Y.-M.; Xu, P.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2019, 84, 11007. |
| [47] | Chen, S.; Oliva, M.; Van Meervelt, L.; Van der Eycken, E. V.; Sharma, U. K. Adv. Synth. Catal. 2021, 363, 3220. |
| [48] | Liu, M.; Wang, X.; Guo, Z.; Li, H.; Huang, W.; Xu, H.; Dai, H.-X. Org. Lett. 2021, 23, 6299. |
| [49] | He, Y.; Wang, Y.; Liang, X.; Huang, B.; Wang, H.; Pan, Y.-M. Org. Lett. 2018, 20, 7117. |
| [50] | Li, M.; Fang, S.; Zheng, J.; Jiang, H.; Wu, W. Org. Lett. 2019, 21, 8439. |
| [51] | Hu, W.; Li, Z.; Li, J.; Wu, W.; Liu, H.; Jiang, H. Adv. Synth. Catal. 2017, 359, 3509. |
| [52] | Li, M.; Zheng, J.; Hu, W.; Li, C.; Li, J.; Fang, S.; Jiang, H.; Wu, W. Org. Lett. 2018, 20, 7245. |
| [53] | Wang, X.; Fu, J. P.; Xie, J. X.; Teng, Q. H.; Tang, H. T.; Pan, Y.-M. Org. Biomol. Chem. 2020, 18, 4936. |
| [54] | Zhu, Y.-M.; Zhang, W.; Li, H.; Xu, X. P.; Ji, S.-J. Adv. Synth. Catal. 2020, 363, 808. |
| [55] | Hu, W.; Li, J.; Xu, Y.; Li, J.; Wu, W.; Liu, H.; Jiang, H. Org. Lett. 2017, 19, 678. |
| [56] | Senadi, G. C.; Lu, T. Y.; Dhandabani, G. K.; Wang, J.-J. Org. Lett. 2017, 19, 1172. |
| [57] | Senadi, G. C.; Guo, B.-C.; Chang, Y.-C.; Hu, W.-P.; Wang, J.-J. Adv. Synth. Catal. 2018, 360, 491. |
| [58] | Wang, X.; Fu, J.-P.; Mo, J.-H.; Tian, Y.-H.; Liu, C.-Y.; Tang, H.-T.; Sun, Z.-J.; Pan, Y.-M. Adv. Synth. Catal. 2021, 363, 2762. |
| [59] | Chu, H.; Dai, Q.; Jiang, Y.; Cheng, J. J. Org. Chem. 2017, 82, 8267. |
| [60] | Liu, Z.; Cao, S.; Wu, J.; Zanoni, G.; Sivaguru, P.; Bi, X. ACS Catal. 2020, 10, 12881. |
| [61] | Ren, Z.-L.; Kong, H.-H.; Lu, W.-T.; Sun, M.; Ding, M.-W. Tetrahedron 2018, 74, 184. |
| [62] | Wang, F.; Xu, P.; Liu, B.-B.; Wang, S.-Y.; Ji, S.-J. Org. Chem. Front. 2019, 6, 3754. |
| [63] | Yuan, W. K.; Liu, Y. F.; Lan, Z.; Wen, L. R.; Li, M. Org. Lett. 2018, 20, 7158. |
| [64] | Collet, J. W.; Morel, B.; Lin, H. C.; Roose, T. R.; Mampuys, P.; Orru, R. V. A.; Ruijter, E.; Maes, B. U. W. Org. Lett. 2020, 22, 914. |
| [65] | Weng, Y.; Zhang, C.; Tang, Z.; Shrestha, M.; Huang, W.; Qu, J.; Chen, Y. Nat. Commun. 2020, 11, 392. |
| [66] | Wang, Y.; Huang, W.; Wang, C.; Qu, J.; Chen, Y. Org. Lett. 2020, 22, 4245. |
| [67] | Huang, W.; Wang, Y.; Weng, Y.; Shrestha, M.; Qu, J.; Chen, Y. Org. Lett. 2020, 22, 3245. |
| [68] | Sugano, K.; Tanase, T.; Kobayashi, K.; Yamamoto, Y. Chem. Lett. 1991, 921. |
| [69] | Ahmadi, F.; Mirzaei, P.; Bazgir, A. Tetrahedron Lett. 2017, 58, 4281. |
| [70] | Gu, Z.-Y.; Liu, C.-G.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem 2017, 82, 2223. |
| [71] | Zou, F.; Chen, X.; Hao, W. Tetrahedron 2017, 73, 758. |
| [72] | Kalsi, D.; Barsu, N.; Dahiya, P.; Sundararaju, B. Synthesis 2017, 49, 3937. |
| [73] | Gu, Z.-Y.; Liu, Y.; Wang, F.; Bao, X.; Wang, S.-Y.; Ji, S.-J. ACS Catal. 2017, 7, 3893. |
| [74] | Jiang, T.; Gu, Z.-Y.; Yin, L.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2017, 82, 7913. |
| [75] | Gu, Z.-Y.; Li, J.-H.; Wang, S.-Y.; Ji, S.-J. Chem. Commun. 2017, |
| [76] | Jiang, S.; Cao, W.-B.; Xu, X.-P.; Ji, S.-J. Org. Lett. 2021, 23, 6740. |
| [77] | Jiang, S.; Cao, W.-B.; Li, H.-Y.; Xu, X.-P.; Ji, S.-J. Green Chem. 2021, 23, 2619. |
| [78] | Gu, Z.-Y.; Han, H.; Li, Z.-Y.; Ji, S.-J.; Xia, J.-B. Org. Chem. Front. 2021, 8, 1544. |
| [79] | Clemenceau, A.; Wang, Q.; Zhu, J. Org. Lett. 2017, 19, 4872. |
| [80] | Burgula, L. N.; Radhakrishnan, K.; Kundu, L. M. Tetrahedron Lett. 2012, 53, 2639. |
| [81] | Liang, H.-W.; Yang, Z.; Jiang, K.; Ye, Y.; Wei, Y. Angew. Chem., Int. Ed. 2018, 57, 5720. |
| [82] | Liu, J.-Q.; Chen, X.; Shen, X.; Wang, Y.; Wang, X.-S.; Bi, X. Adv. Synth. Catal. 2019, 361, 1543. |
| [83] | Meng, X.-H.; Yang, M.; Peng, J.-Y.; Zhao, Y.-L. Adv. Synth. Catal. 2020, 363, 244. |
| [84] | He, X.; Yu, Z.; Zuo, Y.; Yang, C.; Shang, Y. Org. Biomol. Chem. 2017, 15, 7127. |
| [85] | Bu, X.-B.; Wang, Z.; Wang, X.-D.; Meng, X.-H.; Zhao, Y.-L. Adv. Synth. Catal. 2018, 360, 2945. |
| [86] | Bu, X.-B.; Zhang, Z.-X.; Peng, Q.-Q.; Xu, X.; Zhao, Y.-L. J. Org. Chem. 2019, 84, 53. |
| [87] | Yang, Z.; Jiang, K.; Chen, Y.-C.; Wei, Y. J. Org. Chem. 2019, 84, 3725. |
| [88] | Collet, J. W.; Van Der Nol, E. A.; Roose, T. R.; Maes, B. U. W.; Ruijter, E.; Orru, R. V. A. J. Org. Chem. 2020, 85, 7378. |
/
| 〈 |
|
〉 |
