基于C—H键断裂的多氯烷基化反应研究进展
收稿日期: 2022-11-16
修回日期: 2023-02-09
网络出版日期: 2023-03-07
基金资助
国家自然科学基金基金(21801023); 长沙市科技局项目(kq2004070); 电力与交通材料保护湖南省重点实验室(2020CL03)
Research Progress of Polychloroalkylation Based on C—H Bond Cleavage
Received date: 2022-11-16
Revised date: 2023-02-09
Online published: 2023-03-07
Supported by
National Natural Science Foundation of China(21801023); Changsha Municipal Science and Technology Project(kq2004070); Hunan Provincial Key Laboratory of Materials Protection for Electric Power and Transportation(2020CL03)
多氯代烃在有机合成和化学工业, 特别是制药和材料领域中尤其重要, 引起了化学家们的广泛关注, 诞生了各种合成氯代有机化合物的方法. 引入多氯烷基能够作为关键成分改变化合物的药物活性, 同时, 多氯烷基可以作为前体转化为醛、酮和羧酸等具有不同功能性的官能团, 为实现天然产物的后期合成和修饰提供强有力的支持. 通过断裂多氯烷烃中的C—H键来构建多氯代化合物的策略, 由于具有高步骤经济性, 已成为化学家们的研究热点, 取得了重要的研究进展. 总结了利用二氯甲烷、三氯甲烷作为多氯烷基的前体, 从不同的反应体系(过渡金属催化、可见光介导、无金属参与)出发, 综述了近十年来基于C—H键断裂策略的多氯烷基化反应的相关工作, 并对反应设计、机理研究、研究展望等给予评述.
黄芬 , 罗维纬 , 周俊 . 基于C—H键断裂的多氯烷基化反应研究进展[J]. 有机化学, 2023 , 43(7) : 2368 -2390 . DOI: 10.6023/cjoc202211018
Polychlorinated hydrocarbons are particularly important in organic synthesis and chemical industries, especially in the fields of pharmaceuticals and materials, which have attracted wide attention of chemists and given birth to various methods for the synthesis of chlorinated organic compounds. The introduction of polychloroalkyl can be used as key component to change the drug activity of the compound. At the same time, polychloroalkyl can be used as precursors to transform into aldehydes, ketones, carboxylic acids and other functional groups with different functions, providing strong support for the realization of late synthesis and modification of natural products. The strategy of constructing polychlorinated compounds by breaking C—H bonds in polychloroalkanes has become a hot research topic among chemists due to its high step economy and has made significant progress in research. In this paper, the use of dichloromethane and trichloromethane as precursors of polychloroalkyl is summarized, starting from different reaction systems (transition metal catalyzed, visible light mediated, metal-free involved), the relevant work of polychloroalkylation reactions based on C—H bond breaking strategy in the last decade is reviewed, and the reaction design, mechanism research, and research prospects are reviewed.
| [1] | Jeschke, P. Pest Manage. Sci. 2010, 66, 10. |
| [2] | Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; Garneau-Tsodikova, S.; Walsh, C. T. Chem. Rev. 2006, 106, 3364. |
| [3] | Unson, M. D.; Rose, C. B.; Faulkner, D. J.; Brinen, L. S.; Steiner, J. R.; Clardy, J. J. Org. Chem. 1993, 58, 6336. |
| [4] | Hughes, G.; Lewis, J. C. Chem. Rev. 2018, 118, 1. |
| [5] | Sadar, M. D. Cancer Res. 2011, 71, 1208. |
| [6] | Gribble, G. W. Heterocycles 2012, 84, 157. |
| [7] | Owusu-Ansah, E.; Durow, A. C.; Harding, J. R.; Jordan, A. C.; O’Connell, S. J.; Willis, C. L. Org. Biomol. Chem. 2011, 9, 265. |
| [8] | Gribble, G. W. J. Chem. Educ. 2004, 81, 1441. |
| [9] | Gu, Z.; Zakarian, A. Angew. Chem., Int. Ed. 2010, 49, 9702. |
| [10] | Nguyen, V.-A.; Willis, C. L.; Gerwick, W. H. Chem. Commun. 2001, 19, 1934. |
| [11] | Flores, B.; Molinski, T. F. Org. Lett. 2011, 13, 3932. |
| [12] | Paul, C.; Pohnert, G. Nat. Prod. Rep. 2011, 28, 186. |
| [13] | Sadar, M. D.; Williams, D. E.; Mawji, N. R.; Patrick, B. O.; Wikanta, T.; Chasanah, E.; Irianto, H. E.; Soest, R. V.; Andersen, R. J. Org. Lett. 2008, 10, 4947. |
| [14] | Orjala, J.; Gerwick, W. H. J. Nat. Prod. 1996, 59, 427. |
| [15] | Xiao, Q.; Young, K.; Zakarian, A. Org. Lett. 2013, 15, 3314. |
| [16] | Ardá, A.; Soengas, R. G.; Nieto, M. I.; Jiménez, C.; Rodríguez, J. Org. Lett. 2008, 10, 2175. |
| [17] | Durow, A. C.; Long, G. C.; O'Connel, S. J.; Willis, C. L. Org. Lett. 2006, 8, 5401. |
| [18] | Fu, X.; Su, J.-Y.; Zeng, L.-M. Chin. J. Chem. 2000, 18, 882. |
| [19] | Kapojos, M. M.; Abdjul, D. B.; Yamazaki, H.; Ohshiro, T.; Rotinsulu, H.; Wewengkang, D. S.; Sumilat, D. A.; Tomoda, H.; Namikoshi, M.; Uchida, R. Bioorg. Med. Chem. Lett. 2018, 28, 1911. |
| [20] | Zada, S. L.; Green, K. D.; Shrestha, S. K.; Herzog, I. M.; Garneau- Tsodikova, S.; Fridman, M. ACS Infect. Dis. 2018, 4, 1121. |
| [21] | Bao, Y.; Wang, G.-Y.; Zhang, Y.-X.; Bian, K.-J.; Wang, X.-S. Chem. Sci. 2018, 9, 2986. |
| [22] | Shimakoshi, H.; Luo, Z.; Inaba, T.; Hisaeda, Y. Dalton Trans. 2016, 45, 10173. |
| [23] | Sharma, P.; Rohilla, S.; Jain, N. J. Org. Chem. 2017, 82, 1105. |
| [24] | Liu, X.; Li, B.; Gu, Z. J. Org. Chem. 2015, 80, 7547. |
| [25] | Brennführer, A.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2009, 48, 4114. |
| [26] | Luo, W.; Jiang, K.; Li, Y.; Jiang, H.; Yin, B. Org. Lett. 2020, 22, 2093. |
| [27] | Kharasch, M. S.; Jensen, E. V.; Urry, W. H. Science 1945, 102, 128. |
| [28] | Vaillancourt, F. H.; Yeh, E.; Vosburg, D. A.; O’Connor, S. E.; Walsh, C. T. Nature 2005, 436, 1191. |
| [29] | Liang, Y.-Y.; Lv, G.-F.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Adv. Synth. Catal. 2021, 363, 290. |
| [30] | Huang, G.; Yu, J.-T.; Pan, C.-D. Adv. Synth. Catal. 2021, 363, 305. |
| [31] | Liu, S.; Su, Y.-L.; Sun, T.-Y.; Doyle, M.P.; Wu, Y.-D.; Zhang, X. J. Am. Chem. Soc. 2021, 143, 13195. |
| [32] | Lu, M.-Z.; Loh, T.-P. Org. Lett. 2014, 16, 4698. |
| [33] | Chan, C.-W.; Lee, P.-Y.; Yu, W.-Y. Terahedron Lett. 2015, 56, 2559. |
| [34] | Li, X.; Xu, J.; Gao, Y.; Fang, H.; Tang, G.; Zhao, Y. J. Org. Chem. 2015, 80, 2621. |
| [35] | Li, W.-Y.; Wu, C.-S.; Wang, Z.; Yang, L. Chem. Commun. 2018, 54, 11013. |
| [36] | Xu, L.; Chen, J.; Chu, L. Org. Chem. Front. 2019, 6, 512. |
| [37] | Liang, Y.-Y.; Huang, J.; Ouyang, X.-H.; Qin, J.-H.; Song, R.-J.; Li, J.-H. Chem. Commun. 2021, 57, 3684. |
| [38] | Zhao, Z.-W.; Ran, Y.-S.; Hou, Y.-J.; Chen, X.; Ding, X.-L.; Zhang, C.; Li, Y.-M. J. Org. Chem. 2022, 87, 4183. |
| [39] | Zhang, J.-H.; Jiang, L.-L.; Hu, S.-J.; Li, J.-Z.; Yu, X.-C.; Liu, F.-L.; Guan, Y.-T.; Lei, K.-W.; Wei, W.-T. Org. Biomol. Chem. 2022, 20, 7067. |
| [40] | Luo, W.; Jiang, K.; Yin, B. Chin. J. Chem. 2022, 40, 2893. |
| [41] | Liu, Y.; Zhang, J.-L.; Song, R.-J.; Li, J.-H. Eur. J. Org. Chem. 2014, 2014, 1177. |
| [42] | Liu, Y.; Zhang, J.-L.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2014, 1, 1289. |
| [43] | Liu, Y.; Song, R.-J.; Luo, S.; Li, J.-H. Org. Lett. 2018, 20, 212. |
| [44] | Huang, J.; Liang, Y.-Y.; Ouyang, X.-H.; Xiao, Y.-T.; Qin, J.-H.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2021, 8, 7009. |
| [45] | Wang, T.-L.; Zhang, B.-S.; Liu, J.-J.; Liu, X.-J.; Wang, X.-C.; Quan, Z.-J. Org. Chem. Front. 2022, 9, 1004. |
| [46] | Ma, N.; Guo, L.; Shen, Z.-J.; Qi, D.; Yang, C.; Xia, W. Org. Biomol. Chem. 2022, 20, 1731. |
| [47] | Behr, J.-B.; Chavaria, D.; Plantier-Royon, R. J. Org. Chem. 2013, 78, 11477. |
| [48] | Tian, Y.; Liu, Z.-Q. RSC Adv. 2014, 4, 64855. |
| [49] | Ueda, M.; Doi, N.; Miyagawa, H.; Sugita, S.; Takeda, N.; Shinada, T.; Miyata, O. Chem. Commun. 2015, 51, 4204. |
| [50] | Sheng, W.-J.; Jin, C.-A.; Shan, S.; Jia, Y.-X.; Gao, J.-R. Chin. J. Org. Chem. 2016, 36, 325 (in Chinese). |
| [50] | (盛卫坚, 金城安, 单尚, 贾义霞, 高建荣, 有机化学, 2016, 36, 325.) |
| [51] | Xu, J.-K.; Li, S.-J.; Wang, H.-Y.; Xu, W.-C.; Tian, S.-K. Chem. Commun. 2017, 53, 1708. |
| [52] | Pan, C.; Gao, D.; Yang, Z.; Wu, C.; Yu, J.-T. Org. Biomol. Chem. 2018, 16, 5752. |
| [53] | Li, W.-L.; Sun, Y.-T.; Yao, Y.-C.; Xu, Y.; Li, P.; Liu, Y.-J.; Liang, D.-Q. Chin. J. Org. Chem. 2019, 39, 1727 (in Chinese). |
| [53] | (李文兰, 孙一茼, 姚永超, 许颖, 李鹏, 刘颖杰, 梁德强, 有机化学, 2019, 39, 1727.) |
| [54] | Pan, C.; Wu, C.; Yuan, C.; Yu, J.-T. Tetrahedron Lett. 2020, 61, 151499. |
| [55] | Sun, M.; Xu, Z.; Li, W.; Yang, L.; You, H.; Yu, D.; Fang, F.; Wang, Y.; Liu, Z.-Q. Adv. Synth. Catal. 2020, 362, 2195. |
| [56] | Ge, Y.-X.; Yan, Q.-Q.; Tian, Y.-F.; Wang, H.-J.; Zhang, C.-F.; Li, Z.-J. Chin. J. Org. Chem. 2021, 41, 3106 (in Chinese). |
| [56] | (葛雅欣, 闫芹芹, 田云飞, 王海军, 张春芳, 李泽江, 有机化学, 2021, 41, 3106.) |
| [57] | Ren, Y.; Ge, Y.; Yan, Q.; Chen, S.; Li, Y.; Li, L.; Liu, Z.-Q.; Li, Z.-J. J. Org. Chem. 2021, 86, 12460. |
| [58] | Peng, C.-C.; Long, F.; Hu, Y.-C.; Zhou, Z.-R.; Zhang, K.-Y.; Wang, R.; Ye, M.-H.; Xiao, H.-B.; Wu, L.-J. J. Org. Chem. 2022, 87, 2740. |
| [59] | Liu, H.; Yang, Z.; Yu, J.-T.; Pan, C. Adv. Synth. Catal. 2022, 364, 1085. |
| [60] | Shan, Y.; Yang, Z.; Yu, J.-T.; Pan, C. Org. Biomol. Chem. 2022, 20, 5259. |
| [61] | Li, J.-N.; Li, Z.-J.; Shen, L.-Y.; Li, P.; Zhang, Y.; Yang, W.-C. Org. Biomol. Chem. 2022, 20, 6659. |
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