Chinese Journal of Organic Chemistry >
Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process
Received date: 2022-12-28
Revised date: 2023-01-23
Online published: 2023-02-07
Supported by
National Natural Science Foundation of China(22261026)
Thiocyano and selenocyano are both important functional groups with broad application in organic synthesis. Such functional structures also occur frequently in molecules possessing valuable biological and pharmaceutical activities, optical functions, and catalytic profiles. Therefore, developing synthetic methods toward diverse organo thio-/selenocyanates as well as the tandem annulation for the construction of diverse heterocyclic scaffolds keep receiving high interests. The advances on the synthesis of organo thio-/selenocyanates via transition metal-free C—H thiocyanation or selenocyanation as well as the tandem annulation reactions based on such C—H functionalization are reviewed.
Zhongrong Xu , Jieping Wan , Yunyun Liu . Transition Metal-Free C—H Thiocyanation and Selenocyanation Based on Thermochemical, Photocatalytic and Electrochemical Process[J]. Chinese Journal of Organic Chemistry, 2023 , 43(7) : 2425 -2446 . DOI: 10.6023/cjoc202212035
| [1] | (a) Bayarmagnai, B.; Matheis, C.; Jouvin, K.; Goossen, L. J. Angew. Chem., nt. Ed. 2015, 54, 5753. |
| [1] | (b) Brown, S. P.; Smith III, A. B. J. Am. Chem. Soc. 2015, 137, 4034. |
| [1] | (c) Karmaker, P. G.; Huo, F. Asian J. Org. Chem. 2022, 11, e202200226. |
| [1] | (d) Zhang, L.; Niu, C.; Yang, X.; Qin, H.; Yang, J.; Wen, J.; Wang, H. Chin. J. Org. Chem. 2020, 40, 1117 (in Chinese). |
| [1] | (张龙菲, 牛聪, 杨晓婷, 秦宏云, 杨建静, 文江伟, 王桦, 有机化学, 2020, 40, 1117.) |
| [2] | (a) Dean, L. J.; Prinsep, M. R. Nat. Prod. Rep. 2017, 34, 1359. |
| [2] | (b) Elhalem, E.; Bailey, B. N.; Docampo, R.; Ujvary, I.; Szajnman, S. H. J. Med. Chem. 2002, 45, 3984. |
| [2] | (c) Gharbi, C.; Toumi, B.; Soudani, S.; Lefebvre, F.; Kaminsky, W.; Jelsch, C.; Nasr, C. B.; Khedhiri, L. J. Mol. Struct. 2022, 1257, 132620. |
| [2] | (d) Fichtner, I.; Claffey, J.; Deally, A.; Gleeson, B.; Hogan, M.; Markelova, M. R.; Müller-Bunz, H.; Weber, H.; Tacke, M. J. Organomet. Chem. 2010, 695, 1175. |
| [2] | (e) Nie, Y.; Zhong, M.; Li, S.; Li, X.; Zhang, Y.; Zhang, Y.; He, X. Chem. Biodiversity 2020, 17, e1900603. |
| [3] | (a) Kim, H.; Lee, Y. H.; Lyu, T.; Yoo, J. H.; Park, T.; Oh, J. J. Mater. Chem. A 2018, 6, 18173. |
| [3] | (b) Wijejasinghe, N.; Tseteris, L.; Regoutz, A.; Sit, W.-Y.; Fei, Z.; Du, T.; Wang, X.; McLachlan, M. A.; Vourlias, G.; Patsalas, P. A.; Payne, D. J.; Heeney, M.; Anthopoulos, T. D. Adv. Funct. Mater. 2018, 28, 1707319. |
| [3] | (c) Cui, Y.; Zhang, J.; Zhang, G.; Huang, J.; Liu, P.; Antonietti, M.; Wang, X. J. Mater. Chem. 2011, 21, 13032. |
| [4] | (a) Andreev, I. A.; Ratmanova, N. K.; Augustin, A. U.; Ivanova, O. A.; Levina, I. I.; Khrustalev, V. N.; Werz, D. B.; Trushkov, I. V. Angew. Chem., nt. Ed. 2021, 60, 7927. |
| [4] | (b) Shu, C.; Chen, Y.; Yang, X.-D.; Liu, Y.; Chong, S.; Fang, Y.; Liu, Y.; Yang, W.-H. J. Power Sources 2018, 376, 161. |
| [5] | (a) Viger-Gravel, J.; Korobkov, I.; Bryce, D. L. Cryst. Growth Des. 2011, 11, 4984. |
| [5] | (b) Salaudeen, A. A.; Limner, C. A.; Halcrow, M. A. Polyhedron 2008, 27, 2569. |
| [5] | (c) Mochida, T.; Maekawa, S.; Sumitani, R. Inorg. Chem. 2021, 60, 12386. |
| [6] | (a) Yu, J.-T.; Teng, F.; Cheng, J. Adv. Synth. Catal. 2017, 359, 26. |
| [6] | (b) Wang, Z.; Liu, R.; Qu, C.; Zhao, X.-E.; Lv, Y.; Yue, H.; Wei, W. Org. Chem. Front. 2022, 9, 3565. |
| [6] | (c) Nauth, A. M.; Opatz, T. Org. Biomol. Chem. 2019, 17, 11. |
| [7] | (a) Bera, A.; Kabadwal, L. M.; Bera, S.; Banerjee, D. Chem. Commun. 2022, 58, 10. |
| [7] | (b) Feng, Y.-L.; Shi, B.-F. Chin. J. Org. Chem. 2021, 41, 3753 (in Chinese). |
| [7] | (冯亚岚, 史炳锋, 有机化学, 2021, 41, 3753.) |
| [7] | (c) Liu, L.; Duan, X.-H.; Guo, L.-N. Synthesis 2021, 53, 4375. |
| [7] | (d) Pandit, S.; Maiti, S.; Maiti, D. Org. Chem. Front. 2021, 8, 4349. |
| [7] | (e) Peng, K.; Dong, Z.-B. Adv. Synth. Catal. 2021, 363, 1185. |
| [7] | (f) Singh, P.; Chouhan, K. K.; Mukherjee, A. Chem.-Asian J. 2021, 16, 2392. |
| [7] | (g) Wang, C.; Chen, F.; Qian, P.; Cheng, J. Org. Biomol. Chem. 2021, 19, 1705. |
| [7] | (h) Wen, J.; Niu, C.; Yan, K.; Cheng, X.; Gong, R.; Li, M.; Guo, Y.; Yang, J.; Wang, H. Green Chem. 2020, 22, 1129. |
| [8] | For a few recent references, see: (a) Chen, D.; Jiang, J.; Wan, J. -P. Chin. J. Chem. 2022, 40, 2582. |
| [8] | (b) Chen, J.-Y.; Huang, J.; Sun, K.; He, W.-M. Org. Chem. Front. 2022, 9, 1152. |
| [8] | (c) Zhang, Z.; Liu, X.; Zong, X.; Yuan, Y.; Liu, S.; Zhang, T.; Wu, Z.; Yang, J.; Jia, Z. Chin. J. Org. Chem. 2021, 41, 52 (in Chinese). |
| [8] | (张振国, 刘笑笑, 宗鑫龙, 苑亚林, 刘双磊, 张婷, 吴子尚, 杨静莹, 贾振华, 有机化学, 2021, 41, 52.) |
| [8] | (d) Kiran; Rani, P.; Chahal, S.; Sindhu, J.; Kumar, S.; Varma, R. S.; Singh, R. New J. Chem. 2021, 45, 18722. |
| [8] | (e) Yu, Q.; Liu, Y.; Wan, J.-P. Chin. Chem. Lett. 2021, 32, 3514. |
| [8] | (f) Zhang, X.-J.; Wang, Z.; Zhang, H.; Gao, J.-J.; Yang, K.-R.; Fan, W.-Y.; Wu, R.-X.; Feng, M.-L.; Zhu, W.; Zhu, Y.-P. J. Org. Chem. 2022, 87, 835. |
| [8] | (g) Tian, S.; Wang, C.; Xia, J.; Wan, J.-P.; Liu, Y. Adv. Synth. Catal. 2021, 363, 4627. |
| [8] | (h) Wang, X.; Lei, J.; Guo, S.; Zhang, Y.; Ye, Y.; Tang, S.; Sun, K. Chem. Commun. 2022, 58, 1526. |
| [9] | Fotouhi, L.; Nikoofar, K. Tetrahedron Lett. 2013, 54, 2903. |
| [10] | Akhlaghinia, B.; Pourali, A.-R.; Rahmani, M. Synth. Commun. 2012, 42, 1184. |
| [11] | Zhang, X.; Wang, C.; Jiang, H.; Sun, L. RSC Adv. 2018, 8, 22042. |
| [12] | Muniraj, N.; Dhineshkumar, J.; Prabhu, K. R. ChemistrySelect 2016, 1, 1033. |
| [13] | Zhang, H.; Wei, Q.; Wei, S.; Qu, J.; Wang, B. Eur. J. Org. Chem. 2016, 2016, 3373. |
| [14] | Wang, C.; Wang, Z.; Wang, L.; Chen, Q.; He, M. Chin. J. Chem. 2016, 34, 1081. |
| [15] | Khalili, D. New J. Chem. 2016, 40, 2547. |
| [16] | Wang, Z.; Wang, L.; Chen, Q.; He, M.-Y. Synth. Commun. 2018, 48, 76. |
| [17] | Wu, D.; Qiu, J.; Karmaker, P. G.; Yin, H.; Chen, F.-X. J. Org. Chem. 2018, 83, 1576. |
| [18] | Li, C.; Long, P.; Wu, H.; Yin, H.; Chen, F.-X. Org. Biomol. Chem. 2019, 17, 7131. |
| [19] | Yang, Z.; He, J.; Wei, Y.; Li, W.; Liu, P.; Zhao, J.; Wei, Y. Org. Biomol. Chem. 2020, 18, 9088. |
| [20] | Ren, Y.-L.; Wang, W.; Zhao, B.; Tian, X.; Zhao, S.; Wang, J.; Li, F. ChemCatChem 2016, 8, 3361. |
| [21] | Mete, T. B.; Khopade, T. M.; Bhat, R. G. Tetrahedron Lett. 2017, 58, 415. |
| [22] | Ito, Y.; Touyama, A.; Uku, M.; Egami, H.; Hamashima, Y. Chem. Pharm. Bull. 2019, 67, 1015. |
| [23] | Kokorekin, V. A.; Yaubasarova, R. R.; Neverov, S. V.; Petrosyan, V. A. Eur. J. Org. Chem. 2019, 2019, 4233. |
| [24] | Fan, W.; Yang, Q.; Xu, F.; Li, P. J. Org. Chem. 2014, 79, 10588. |
| [25] | Zhang, W.; Tang, J.; Yu, W.; Huang, Q.; Fu, Y.; Kuang, G.; Pan, C.; Yu, G. ACS Catal. 2018, 8, 8084. |
| [26] | Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275. |
| [27] | He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1895. |
| [28] | Singh, M.; Yadav, L. D. S.; Singh, R. K. P. Tetrahedron Lett. 2020, 61, 151700. |
| [29] | Yi, B.; Wen, X.; Yi, Z.; Xie, Y.; Wang, Q.; Tan, J.-P. Tetrahedron Lett. 2020, 61, 152628. |
| [30] | Koohgard, M.; Hosseinpour, Z.; Sarvestani, A. M.; Hosseini- Sarvari, M. Catal. Sci. Technol. 2020, 10, 1401. |
| [31] | Sahu, K.; Mondal, S.; Mobin, S. M.; Kar, S. J. Org. Chem. 2021, 86, 3324. |
| [32] | Yang, D.; Yan, K.; Wei, W.; Li, G.; Lu, S.; Zhao, C.; Tian, L.; Wang, H. J. Org. Chem. 2015, 80, 11073. |
| [33] | Songsichan, T.; Katrun, P.; Khaikate, O.; Soorukram, D.; Pohmakotr, M.; Reutrakul, V.; Kuhakarn, C. SynOpen 2018, 2, 6. |
| [34] | Dai, P.; Li, C.; Li, Y.; Xia, Q.; Zhang, M.; Gu, Y.-C.; Zhang, W.-H. Asian J. Org. Chem. 2020, 9, 1585. |
| [35] | Filho, E. O. L.; Malvestiti, I. ACS Omega 2020, 5, 33329. |
| [36] | Zhu, Y.-S.; Xue, Y.; Liu, W.; Zhu, X.; Hao, X.-Q.; Song, M.-P. J. Org. Chem. 2020, 85, 9106. |
| [37] | Abonia, R.; Gutierrez, L. F.; Zwarycz, A. T.; Smits, S. C.; Laali, K. K. Heteroatom Chem. 2019, 2019, 1459681. |
| [38] | Li, H.; Chen, P.; Wu, Z.; Lu, Y.; Peng, J.; Chen, J.; He, W. Chin. J. Org. Chem. 2022, 42, 3398 (in Chinese). |
| [38] | (李红霞, 陈棚, 伍智林, 陆雨函, 彭俊梅, 陈锦杨, 何卫民, 有机化学, 2022, 42, 3398.) |
| [39] | Zhang, X. Z.; Ge, D. L.; Chen, S. Y.; Yu, X. Q. RSC Adv. 2016, 6, 66320. |
| [40] | Ghosh, P.; Chhetri, G.; Nandi, A. K.; Sarkar, S.; Saha, T.; Das, S. New J. Chem. 2019, 43, 10959. |
| [41] | Sorabad, G. S.; Maddani, M. R. New J. Chem. 2020, 44, 2222. |
| [42] | Chen, X.-B.; Wang, X.-Q.; Song, J.-N.; Yang, Q.-L.; Huang, C.; Liu, W. Org. Biomol. Chem. 2017, 15, 3611. |
| [43] | Duan, X.; Liu, X.; Cuan, X.; Wang, L.; Liu, K.; Zhou, H.; Chen, X.; Li, H.; Wang, J. J. Org. Chem. 2019, 84, 12366. |
| [44] | Yang, Z.; Hu, L.; Cao, T.; An, L.; Li, L.; Yang, T.; Zhou, C. New J. Chem. 2019, 43, 16441. |
| [45] | Ali, D.; Panday, A. K.; Choudhury, L. H. J. Org. Chem. 2020, 85, 13610. |
| [46] | Gao, Y.; Liu, Y.; Wan, J.-P. J. Org. Chem. 2019, 84, 2243. |
| [47] | Zeng, J.; Wan, J.-P.; Liu, Y. J. Org. Chem. 2022, 87, 13195. |
| [48] | Chauhan, P.; Ritu; Preeti; Kumar, S.; Jain, N. Eur. J. Org. Chem. 2019, 2019, 4334. |
| [49] | Li, G.; Yan, Q.; Gong, X.; Dou, X.; Yang, D. ACS Sustainable Chem. Eng. 2019, 7, 14009. |
| [50] | Lu, F.; Zhang, K.; Yao, Y.; Yin, Y.; Chen, J.; Zhang, X.; Wang, Y.; Lu, L.; Gao, Z.; Lei, A. Green Chem. 2021, 23, 763. |
| [51] | Chen, Q.; Lei, Y.; Wang, Y.; Wang, C.; Wang, Y.; Xu, Z.; Wang, H.; Wang, R. Org. Chem. Front. 2017, 4, 369. |
| [52] | Wen, J.; Zhang, L.; Yang, X.; Niu, C.; Wang, S.; Wei, W.; Sun, X.; Yang, J.; Wang, H. Green Chem. 2019, 21, 3597. |
| [53] | Sun, K.; Lv, Y.; Chen, Y.; Zhou, T.; Xing, Y.; Wang, X. Org. Biomol. Chem. 2017, 15, 4464. |
| [54] | Cui, J.; Wei, M.; Pang, L.; Xiao, J.; Gan, C.; Guo, J.; Xie, C.; Zhu, Q.; Huang, Y. Tetrahedron 2020, 76, 130978. |
| [55] | Liang, S.; Zeng, C.-C.; Tian, H.-Y.; Sun, B.-G.; Luo, X.-G.; Ren, F.-Z. Adv. Synth. Catal. 2018, 360, 1444. |
| [56] | Xiao, J.-A.; Li, Y.-C.; Cheng, X.-L.; Chen, W.-Q.; Cui, J.-G.; Huang, Y.-M.; Huang, J.; Xiao, Q.; Su, W.; Yang, H. Org. Chem. Front. 2019, 6, 1967. |
| [57] | Mao, X.; Ni, J.; Xu, B.; Ding, C. Org. Chem. Front. 2020, 7, 350. |
| [58] | Kang, L.-S.; Luo, M.-H.; Lam, C. M.; Hu, L.-M.; Little, R. D.; Zeng, C.-C. Green Chem. 2016, 18, 3767. |
| [59] | Yuan, P.-F.; Zhang, Q.-B.; Jin, X.-L.; Lei, W.-L.; Wu, L.-Z.; Liu, Q. Green Chem. 2018, 20, 5464. |
| [60] | Qiu, J.; Wu, D.; Karmaker, P. G.; Yin, H.; Chen, F.-X. Org. Lett. 2018, 20, 1600. |
| [61] | Qiu, J.; Wu, D.; Yuan, L.; Long, P.; Yin, H.; Chen, F.-X. J. Org. Chem. 2019, 84, 7917. |
| [62] | Yadav, A. K.; Yadav, L. D. S. Tetrahedron Lett. 2015, 56, 6696. |
| [63] | Wu, D.; Duan, Y.; Liang, K.; Yin, H.; Chen, F.-X. Chem. Commun. 2021, 57, 9938. |
| [64] | Liu, D.; Zhang, Z.; Yu, J.; Chen, H.; Lin, X.; Li, M.; Wen, L.; Guo, W. Org. Chem. Front. 2022, 9, 2963. |
| [65] | Maeda, B.; Aihara, Y.; Sato, A.; Kinoshita, T.; Murakami, K. Org. Lett. 2022, 24, 7366. |
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