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2020 , Vol. 40 >Issue 2: 454 - 461

DOI: https://doi.org/10.6023/cjoc201907046

研究论文

高价碘试剂介导的8-氨基喹啉C(5)位碳-氢键亲核氟化反应

  • 陈倩雯 ,
  • 杨耀成 ,
  • 王霞 ,
  • 张谦 ,
  • 李栋
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  • 湖北工业大学材料与化学工程学院 武汉 430068

收稿日期: 2019-07-28

  修回日期: 2019-09-19

  网络出版日期: 2019-10-12

基金资助

国家自然科学基金（No.21702054）和大学生创新创业训练计划（No.201610500005）资助项目.

收起

Hypervalent Iodine Reagent-Mediated C(5) C-H Nucleophilic Fluorination of 8-Aminoqunolines

  • Chen Qianwen ,
  • Yang Yaocheng ,
  • Wang Xia ,
  • Zhang Qian ,
  • Li Dong
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  • College of Materials and Chemical Engineering, Hubei University of Technology, Wuhan 430068

Received date: 2019-07-28

  Revised date: 2019-09-19

  Online published: 2019-10-12

Supported by

Project supported by the National Natural Science Foundation of China (No. 21702054) and the Innovation and Entrepreneurship Training Program (No. 201610500005).

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摘要

8-氨基喹啉的C（5）位碳-氢键氟化反应近年来受到广泛关注，但大多需要使用过渡金属催化剂和亲电氟化试剂来实现.在高价碘试剂的介导下实现了无过渡金属催化条件下的8-氨基喹啉C（5）位碳-氢键亲核氟化反应.使用廉价易得且安全稳定的氟化银作为亲核氟化试剂，反应无需惰性气体保护，条件简单，操作方便，区域选择性好，底物范围较广，为喹啉类化合物的氟化提供了一种有潜在应用价值的新方法.

关键词： 高价碘; 8-氨基喹啉; 亲核氟化; 氟化银

本文引用格式

陈倩雯 , 杨耀成 , 王霞 , 张谦 , 李栋 . 高价碘试剂介导的8-氨基喹啉C(5)位碳-氢键亲核氟化反应[J]. 有机化学, 2020 , 40(2) : 454 -461 . DOI: 10.6023/cjoc201907046

Abstract

The C(5) C-H fluorination of 8-aminoqunolines has attracted much attention recently. However, transition-metal catalyst and electrophilic fluorination reagents were required in most of these reactions. Transition-metal catalyst free C(5) C-H nucleophilic fluorination of 8-aminoqunolines was reviewed. This reaction was mediated by a hypervalent iodine reagent and employed cheap, safe and stable silver fluoride as the nucleophilic fluorination reagent. The reaction proceeded without inert gas protection. It possess the merits of simple and mild reaction conditions, easy operation, high regioselectivity and wide substrate scope and provides a novel method for fluorination of quinolines with potential application value.

Key words： hypervalent iodine; 8-aminoqunoline; nucleophilic fluorination; silver fluoride

参考文献

[1] (a) Colomb, J.; Becker, G.; Fieux, S.; Zimmer, L.; Billard, T. J. Med. Chem. 2014, 57, 3884.
(b) Vandekerckhove, S.; Tran, H. G.; Desmet, T.; D'hooghe, M. Bioorg. Med. Chem. Lett. 2013, 23, 4641.
(c) Jiang, H.; Taggart, J. E.; Zhang, X. H. G.; Benbrook, D. M.; Lind, S. E.; Ding, W. Q. Cancer Lett. 2011, 312, 11.
(d) Solomon, V. R.; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
(e) Tokoro, Y.; Nagai, A.; Kokado, K.; Chujo, Y. Macromolecules 2009, 42, 2988.
(f) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(g) Eicher, T.; Hauptmann, S.; Speicher, A. The Chemistry of Heterocycles:Structures, Reactions, Synthesis, and Applications, 3rd ed., John Wiley & Sons, New York, 2013.
(h) Katritzky, A. R.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. Comprehensive Heterocyclic Chemistry III, Elsevier, Oxford, 2008.
[2] (a) Rouquet, G.; Chatani, N. Angew. Chem., Int. Ed. 2013, 52, 11726.
(b) Corbet, M.; De Campo, F. Angew. Chem., Int. Ed. 2013, 52, 9896.
(c) Chen, Z.; Wang, B.; Zhang, J.; Yu, W.; Liu, Z.; Zhang, Y. Org. Chem. Front. 2015, 2, 1107.
(d) Daugulis, O.; Roane, J.; Tran, L. D. Acc. Chem. Res. 2015, 48, 1053.
(e) Yadav, M. R.; Rit, R. K.; Shankar, M.; Sahoo, A. K. Asian J. Org. Chem. 2015, 4, 846.
(f) Liu, J.; Chen, G.; Tan, Z. Adv. Synth. Catal. 2016, 358, 1174.
(g) Rit, R. K.; Yadav, M. R.; Ghosh, K.; Sahoo, A. K. Tetrahedron 2015, 71, 4450.
(h) Zhang, B.; Guan, H.; Liu, B.; Shi, B. Chin. J. Org. Chem. 2014, 34, 1487(in Chinese). (张博, 管晗曦, 刘斌, 史炳锋, 有机化学, 2014, 34, 1487.)
(i) Zhang, W.; Zhang, J.; Liu, Y. Chin. J. Org. Chem. 2014, 34, 36(in Chinese). (张巍, 张家慧, 刘运奎, 有机化学, 2014, 34, 36.)
(j) Dou, Y.; Gu, X.; Jiang, J.; Zhu, Q. Prog. Chem. 2018, 30, 1317(in Chinese). (窦言东, 顾晓旭, 蒋建泽, 朱勍, 化学进展, 2018, 30, 1317.)
[3] (a) Roger, J.; Gottumukkala, A. L.; Doucet, H. ChemCatChem 2010, 2, 20.
(b) Iwai, T.; Sawamura, M. ACS Catal. 2015, 5, 5031.
(c) Stephens, D. E.; Larionov, O. V. Tetrahedron 2015, 71, 8683.
[4] Suess, A. M.; Ertem, M. Z.; Cramer, C. J.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
[5] (a) Zhu, L.; Cao, X.; Li, Y.; Liu, T.; Wang, X.; Qiu, R.; Yin, S.-F. Chin. J. Org. Chem. 2017, 37, 1613(in Chinese). (朱龙志, 曹鑫, 李优, 刘婷, 王勰, 邱仁华, 尹双凤, 有机化学, 2017, 37, 1613.)
(b) Khan, B.; Dutta, H. S.; Koley, D. Asian J. Org. Chem. 2018, 7, 1270.
[6] (a) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305.
(d) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496.
(e) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501.
(f) Walker, M. C.; Chang, M. C. Y. Chem. Soc. Rev. 2014, 43, 6527.
(g) Ni, C.; Hu, J. Chem. Soc. Rev. 2016, 45, 5441.
(h) Qing, F. L.; Qiu, X. L. Organofluorine Chemistry, Science Press, Beijing, 2007(in Chinese). (卿凤翎, 邱小龙, 有机氟化学, 科学出版社, 北京, 2007.)
(i) Kirsch, P. Modern Fluoroorganic Chemistry, Wiley-VCH Verlag GmbH. & KGaA., Weinheim, 2013.
[7] (a) Furuya, T.; Kamlet, A. S.; Ritter, T. Nature 2011, 473, 470.
(b) Jin, Z.; Hammond, G. B.; Xu, B. Aldrichim. Acta 2012, 45, 67.
(c) Liang, T.; Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2013, 52, 8214.
(d) Campbell, M. G.; Ritter, T. Chem. Rev. 2015, 115, 612.
(e) Champagne, P. A.; Desroches, J.; Hamel, J.-D.; Vandamme, M.; Paquin, J.-F. Chem. Rev. 2015, 115, 9073.
(f) Lin, A.; Huehls, C. B.; Yang, J. Org. Chem. Front. 2014, 1, 434.
(g) Ma, J.-A.; Li, S. Org. Chem. Front. 2014, 1, 712.
(h) Li, Y.; Wu, Y.; Li, G.-S.; Wang X.-S. Adv. Synth. Catal. 2014, 356, 1412.
(i) He, J.; Lou, S.; Xu, D. Chin. J. Org. Chem. 2016, 36, 1218(in Chinese). (何将旗, 娄绍杰, 许丹倩, 有机化学, 2016, 36, 1218.)
[8] (a) Ding, J.; Zhang, Y.; Li, J. Org. Chem. Front. 2017, 4, 1528.
(b) Luo, S.-S.; Su, L.-J.; Jiang, Y.; Li, X.-B.; Li, Z.-H.; Sun, H.; Liu, J.-K. Synlett 2018, 29, 1525.
[9] (a) Zhang, Y.; Wen, C.; Li, J. Org. Biomol. Chem. 2018, 16, 1912.
(b) Chen, H.; Li, P.; Wang, M.; Wang, L. Eur. J. Org. Chem. 2018, 2091.
[10] (a) Differding, E.; Ofner, H. Synlett 1991, 187.
(b) Banks, R. E. J. Fluorine Chem. 1998, 87, 1.
[11] (a) Hollingworth, C.; Gouverneur, V. Chem. Commun. 2012, 48, 2929.
(b) Ni, C.; Jiang, F.; Zeng, Y.; Hu, J. J. Fluorine Chem. 2015, 179, 3.
(c) Zeng, Y.; Hu, J. Rep. Org. Chem. 2015, 5, 19.
[12] Wang, Y.; Wang, Y.; Jiang, K.; Zhang, Q.; Li, D. Org. Biomol. Chem. 2016, 14, 10180.
[13] (a) Sen, C.; Sahoo, T.; Ghosh, S. C. ChemistrySelect 2017, 2, 2745.
(b) Jiao, J.-Y.; Mao, Y.-J.; Feng, A.-W.; Li, X.-F.; Li, M.-T.; Zhang, X.-H. Tetrahedron 2017, 73, 1482.
(c) Chen, X.-X.; Wang, J.-X.; Ren, J.-T.; Xie, H.; Zhao, Y.; Li, Y.-M.; Sun, M. Synlett 2017, 28, 1840.
(d) Qiao, L.; Cao, X.; Chai, K.; Shen, J.; Xu, J.; Zhang, P. Tetrahedron Lett. 2018, 59, 2243.
[14] (a) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2002, 102, 2523.
(b) Wirth, T. Angew. Chem., Int. Ed. 2005, 44, 3656.
(c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299.
(d) Yusubov, M. S.; Zhdankin, V. V. Curr. Org. Synth. 2012, 9, 247.
(e) Brown, M.; Farid, U.; Wirth, T. Synlett 2013, 424.
(f) Zhdankin, V. V. Hypervalent Iodine Chemistry, John Wiley & Sons Ltd., New York, 2014.
(g) Kita, Y.; Dohi, T. Chem. Rec. 2015, 15, 886.
(h) Narayan, R.; Manna, S.; Antonchick, A. P. Synlett 2015, 26, 1785.
(i) Muñiz, K. Top. Curr. Chem. 2016, 373, 105.
(j) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
(k) Zhang, X.; Cong, Y.; Lin, G.; Guo, X.; Cao, Y.; Lei, K.; Du, Y. Chin. J. Org. Chem. 2016, 36, 2513(in Chinese). (张翔, 丛颖, 林光宇, 郭旭亮, 曹阳, 雷坤华, 杜云飞, 有机化学, 2016, 36, 2513.)
(l) Budhwan, R.; Yadav, S.; Murarka, S. Org. Biomol. Chem. 2019, 17, 6326.
[15] Duan, Y.; Jiang, S.; Han, Y.; Sun, B.; Zhang, C. Chin. J. Org. Chem. 2016, 36, 1973(in Chinese). (段亚南, 姜山, 韩永超, 孙博, 张弛, 有机化学, 2016, 36, 1973.)
[16] Tian, T.; Zhong, W.; Meng, S.; Meng, X.; Li, Z. J. Org. Chem. 2013, 78, 728.
[17] (a) Wang, Y.; Wang, Y.; Guo, Z.; Zhang, Q.; Li, D. Asian J. Org. Chem. 2016, 5, 1438.
(b) Wang, Y.; Wang, Y.; Zhang, Q.; Li, D. Org. Chem. Front. 2017, 4, 514.
[18] (a) Huang, P.-Q. Acta Chim. Sinica 2018, 76, 357(in Chinese). (黄培强, 化学学报, 2018, 76, 357.)
(b) Huang, Y.-H.; Wang, S.-R.; Wu, D.-P.; Huang, P.-Q. Org. Lett. 2019, 21, 1681.
(c) Zheng, W.; Yang, W.; Luo, D.; Min, L.; Wang, X.; Hu, Y. Adv. Synth. Catal. 2019, 361, 1995.
(d) Li, L.-H.; Niu, Z.-J.; Liang, Y.-M. Chem.-Eur. J. 2017, 23, 15300.
(e) Ye, J.-L.; Zhu, Y.-N.; Geng, H.; Huang, P.-Q. Sci. China, Chem. 2018, 61, 687.
(f) Gao, Y.-J.; Xiao, Z.-H.; Liu, L.-X.; Huang, P.-Q. Chin. J. Org. Chem. 2017, 37, 1189(in Chinese). (高燕娇, 肖振华, 刘良先, 黄培强, 有机化学, 2017, 37, 1189.)
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