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2022 , Vol. 42 >Issue 12: 4078 - 4098

DOI: https://doi.org/10.6023/cjoc202208026

综述与进展

自由基参与的烯烃C—CF3/C—N键形成反应研究进展

  • 郑绿茵 ,
  • 王逸涵 ,
  • 蔡刘欢 ,
  • 郭维
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  • 赣南师范大学江西省有机药物化学重点实验室 江西赣州 341000

收稿日期: 2022-08-20

  修回日期: 2022-09-12

  网络出版日期: 2022-10-14

基金资助

国家自然科学基金(22167002); 国家自然科学基金(21867001)

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Progress in C—CF3/C—N Bond Formation Reactions of Alkenes Involving in Free Radicals

  • Lüyin Zheng ,
  • Yihan Wang ,
  • Liuhuan Cai ,
  • Wei Guo
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  • Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou, Jiangxi 341000
*E-mail: ;

Received date: 2022-08-20

  Revised date: 2022-09-12

  Online published: 2022-10-14

Supported by

National Natural Science Foundation of China(22167002); National Natural Science Foundation of China(21867001)

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摘要

烯烃的双官能团化反应是当前有机合成领域的研究热点. 这些反应可以快速、经济的在烯烃的碳-碳双键(C=C)上引入两个相同或不同的基团, 从而增加分子的复杂性和应用价值. 三氟甲基对有机化合物的亲脂性、渗透性和代谢稳定性等性质有重要影响, 同时C—N键广泛存在于各种有机分子结构中. 通过烯烃的双官能团化同时构建C—CF3和C—N键, 在有机合成和药物化学领域具有重要意义. 按照不同“N”源进行分类, 综述了近年来自由基参与的烯烃C—CF3和C—N键形成反应的研究进展, 阐述了可能经历的自由基化学反应历程, 对其应用前景进行了展望.

关键词： 自由基; 烯烃; 三氟甲基; C—N键

本文引用格式

郑绿茵 , 王逸涵 , 蔡刘欢 , 郭维 . 自由基参与的烯烃C—CF3/C—N键形成反应研究进展[J]. 有机化学, 2022 , 42(12) : 4078 -4098 . DOI: 10.6023/cjoc202208026

Abstract

Bifunctionalization of alkenes is a hot topic in organic synthesis, which can introduce different functional groups into the carbon-carbon double bond (C=C) of olefins quickly and economically, thereby increasing the complexity and application value of molecules. The trifluoromethyl groups can influence lipophilicity, permeability, and metabolic stability of organic compounds. Meanwhile, C—N bond widely exists in various organic molecules. The construction of C—CF3/C—N bond simultaneously through bifunctionalization of alkenes is of great significant in the field of organic synthesis and medicinal chemistry. In this review, we focus on the progress in C—CF3/C—N bond formation reactions of alkenes involving free radical intermediates based on different “N” sources. The possible radical reaction mechanism and their possible applications are also highlighted.

Key words： free radicals; alkenes; trifluoromethyl groups; C—N bond

参考文献

[1]
Hopkins, B. A.; Wolfe, J. P. Angew. Chem., Int. Ed. 2012, 51, 9886.
[2]
(a) Wu, K.; Liang, Y.; Jiao, N. Molecules 2016, 21, 352.
[2]
(b) Yin, G.; Mu, X.; Liu, G. Acc. Chem. Res. 2016, 49, 2413.
[2]
(c) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32.
[3]
(a) Bégué, J.-P.; Bonnet-Delpon, D. J. Fluorine Chem. 2006, 12, 992.
[3]
(b) Wu, X.-F.; Neumann, H.; Beller, M. Chem. Asian J. 2012, 7, 1744.
[3]
(c) Zhang, C. Org. Biomol. Chem. 2014, 12, 6580.
[4]
(a) Kolahdouzan, K.; Kumar, R.; Gaunt, M. J. Chem. Sci. 2020, 11, 12089.
[4]
(b) Duan, P.; Zhao, H.; Yang, J.; Cao, L.; Jiang, H.; Zhang, M. Org. Lett. 2022, 24, 608.
[5]
(a) Bohm, H.-J.; Banner, D.; Bendels, S.; Kansy, M.; Kuhn, B.; Muller, K.; Obst-Sander, U.; Stahl, M. ChemBioChem 2004, 5, 637.
[5]
(b) Kirk, K. L. J. Fluorine Chem. 2006, 127, 1013.
[5]
(c) Swallow, S. Prog. Med. Chem. 2015, 54, 65.
[6]
(a) Yu, J.; Zhou, Y.; Chen, D.-F.; Gong, L.-Z. Pure Appl. Chem. 2014, 86, 1217.
[6]
(b) Suliman, R. S.; Alghamdi, S. S.; Ali, R.; Rahman, I.; Alqahtani, T.; Frah, I. K.; Aljatli, D. A.; Huwaizi, S.; Algheribe, S.; Alehaideb, Z.; Islam, I. Molecules 2022, 27, 2409.
[6]
(c) Sasidharan, N.; Kumar, A. S.; Hng, H. H. ChemistrySelect 2018, 3, 12544.
[7]
Chen, X.; Xiao, F.; He, W.-M. Org. Chem. Front. 2021, 8, 5206.
[8]
(a) Egami, H.; Sodeoka, M. Angew. Chem., Int. Ed. 2014, 53, 8294.
[8]
(b) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598.
[9]
Koike, T. Asian J. Org. Chem. 2020, 9, 529.
[10]
(a) Chen, D.; Yang, W.; Yao, Y.; Yang, X.; Deng, Y.; Yang, D. Chin. J. Org. Chem. 2018, 38, 2571. (in Chinese)
[10]
( 陈董涵, 杨文, 姚永祺, 杨新, 邓颖颖, 杨定乔, 有机化学, 2018, 38, 2571.)
[10]
(b) Qiu, Y.; Wei, F.; Ye, L.; Zhao, M. Chin. J. Org. Chem. 2021, 41, 1821. (in Chinese)
[10]
( 邱云亮, 魏凤姣, 叶鎏, 赵旻玥, 有机化学, 2021, 41, 1821.)
[11]
Xiao, H.; Shen, H.; Zhu, L.; Li, C. J. Am. Chem. Soc. 2019, 141, 11440.
[12]
(a) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048.
[12]
(b) Zheng, L.; Cai, L.; Tao, K.; Xie, Z.; Lai, Y.-L.; Guo, X. Asian J. Org. Chem. 2021, 10, 711.
[12]
(c) Zheng, L.; Tao, K.; Guo, W. Adv. Synth. Catal. 2021, 363, 62.
[13]
Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136.
[14]
Noto, N.; Koike, T.; Akita, M. Chem. Sci. 2017, 8, 6375.
[15]
Xiong, Y.; Ma, X.; Zhang, G. Org. Lett. 2019, 21, 1699.
[16]
Ge, H.; Wu, B.; Liu, Y.; Wang, H.; Shen, Q. ACS Catal. 2020, 10, 12414.
[17]
Zhang, L.; Zhang, G.; Wang, P.; Li, Y.; Lei, A. Org. Lett. 2018, 20, 7396.
[18]
Huang, Y.; Hong, H.; Zou, Z.; Liao, C.; Lu, J.; Qin, Y.; Li, Y.; Chen, L. Org. Biomol. Chem. 2019, 17, 5014.
[19]
Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. Angew. Chem., Int. Ed. 2014, 53, 1881.
[20]
Yang, M.; Wang, W.; Liu, Y.; Feng, L.; Ju, X. Chin. J. Chem. 2014, 32, 833.
[21]
Xiong, Y.; Sun, Y.; Zhang, G. Org. Lett. 2018, 20, 6250.
[22]
Wu, L.; Zhang, Z.; Wu, D.; Wang, F.; Chen, P.; Lin, Z.; Liu, G. Angew. Chem., Int. Ed. 2021, 60, 6997.
[23]
Karimov, R. R.; Sharma, A.; Hartwig, J. F. ACS Cent. Sci. 2016, 2, 715.
[24]
Zhu, C.-L.; Wang, C.; Qin, Q.-X.; Yruegas, S.; Martin, C. D.; Xu, H. ACS Catal. 2018, 86, 5032.
[25]
Xiong, H.; Ramkumar, N.; Chiou, M.-F.; Jian, W.; Li, Y.; Su, J.-H.; Zhang, X.; Bao, H. Nat. Commun. 2019, 10, 122.
[26]
Ge, L.; Zhou, H.; Chiou, M.-F.; Jiang, H.; Jian, W.; Ye, C.; Li, X.; Zhu, X.; Xiong, H.; Li, Y.; Song, L.; Zhang, X.; Bao, H. Nat. Catal. 2021, 4, 28.
[27]
Liu, W.; Pu, M.; He, J.; Zhang, T.; Dong, S.; Liu, X.; Wu, Y.-D.; Feng, X. J. Am. Chem. Soc. 2021, 143, 11856.
[28]
Zhang, Y.; Han, X.; Zhao, J.; Qian, Z.; Li, T.; Tang, Y.; Zhang, H.-Y. Adv. Synth. Catal. 2018, 360, 2659.
[29]
Huang, H.-G.; Li, W.; Zhong, D.; Wang, H.-C.; Zhao, J.; Liu, W.-B. Chem. Sci. 2021, 12, 3210.
[30]
Carboni, A.; Dagousset, G.; Magnier, E.; Masson, G. Org. Lett. 2014, 16, 1240.
[31]
Dagousset, G.; Carboni, A.; Magnier, E.; Masson, G. Org. Lett. 2014, 16, 4340.
[32]
Geng, X.; Lin, F.; Wang, X.; Jiao, N. Org. Lett. 2017, 19, 4738.
[33]
Liu, H.; Guo, Q.; Chen, C.; Wang, M.; Xu, Z. Org. Chem. Front. 2018, 5, 1522.
[34]
Zhang, M.; Lin, J.-H.; Xiao, J.-C. Org. Lett. 2021, 23, 6079.
[35]
Yu, X.-L.; Chen, J.-R.; Chen, D.-Z.; Xiao, W.-J. Chem. Commun. 2016, 52, 8275.
[36]
Wang, P.; Zhu, S.; Lu, D.; Gong, Y. Org. Lett. 2020, 22, 1924.
[37]
Egami, H.; Kawamura, S.; Miyazaki, A.; Sodeoka, M. Angew. Chem., Int. Ed. 2013, 52, 7841.
[38]
Lin, J.-S.; Xiong, Y.-P.; Ma, C.-L.; Zhao, L.-J.; Tan, B.; Liu, X.-Y. Chem.-Eur. J. 2014, 20, 1332.
[39]
Lin, J.-S.; Dong, X.-Y.; Li, T.-T.; Jiang, N.-C.; Tan, B.; Liu, X.-Y. J. Am. Chem. Soc. 2016, 138, 9357.
[40]
Lin, J.-S.; Wang, F.-L.; Dong, X.-Y.; He, W.-W.; Yuan, Y.; Chen, S.; Liu, X.-Y. Nat. Commun. 2017, 8, 14841.
[41]
Zhang, H.-Y.; Huo, W.; Ge, C.; Zhao, J.; Zhang, Y. Synlett 2017, 28, 962.
[42]
Chang, B.; Su, Y.; Huang, D.; Wang, K.-H.; Zhang, W.; Shi, Y.; Zhang, X.; Hu, Y. J. Org. Chem. 2018, 83, 4365.
[43]
Mou, X.-Q.; Rong, F.-M.; Zhang, H.; Chen, G.; He, G. Org. Lett. 2019, 21, 4657.
[44]
Kim, E.; Choi, S.; Kim, H.; Cho, E. J. Chem.-Eur. J. 2013, 19, 6209.
[45]
Wei, Q.; Chen, J.-R.; Hu, X.-Q.; Yang, X.-C.; Lu, B.; Xiao, W.-J. Org. Lett. 2015, 17, 4464.
[46]
Noto, N.; Miyazawa, K.; Koike, T.; Akita, M. Org. Lett. 2015, 17, 3710.
[47]
Jarrige, L.; Carboni, A.; Dagousset, G.; Levitre, G.; Magnier, E.; Masson, G. Org. Lett. 2016, 18, 2906.
[48]
Claraz, A.; Djian, A.; Masson, G. Org. Chem. Front. 2021, 8, 288.
[49]
Claraz, A.; Courant, T.; Masson, G. Org. Lett. 2020, 22, 1580.
[50]
Zheng, Y.-N.; Zheng, H.; Li, T.; Wei, W.-T. ChemSusChem 2021, 14, 5340.
[51]
Proctor, P. S. J.; Colgan, A. C.; Phipps, R. J. Nat. Chem. 2020, 12, 990.
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