基于I2催化的C-H键功能团化的研究进展
收稿日期: 2019-04-10
修回日期: 2019-04-24
网络出版日期: 2019-04-11
基金资助
国家自然科学基金（Nos.21602064，21572072）、泉州市科技计划项目（No.2018C073R）、华侨大学研究生科研创新基金资助项目.
Recent Advances in the I2-Catalyzed C-H Bond Functionalizations
Received date: 2019-04-10
Revised date: 2019-04-24
Online published: 2019-04-11
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21602064, 21572072), the Science and Technology Project of Quanzhou City (No. 2018C073R), and the Postgraduates Innovative Fund in Scientific Research of Huaqiao University.
施兆江 , 王连会 , 崔秀灵 . 基于I2催化的C-H键功能团化的研究进展[J]. 有机化学, 2019 , 39(6) : 1596 -1612 . DOI: 10.6023/cjoc201902001
Heterocyclic compounds are widely applied in medicine, fine chemical engineering and the related industrial fields. Consequently, the development of efficient strategies for heterocycle constructions continues to be of great appeal in organic synthesis. In recent years, the I2-catalyzed direct C-H bond functionalizations have emerged as one of the most efficient synthetic protocols to construct diverse heterocycles. In this review, the recent advances in I2-catalyzed C-H bond functionalizations by the types of C-C and C-N/O/S bond formations are summarized, and an outlook of this research filed is given.
Key words： I2-catalysis; C-H bond activation; heterocycles
[1] (a) Yang, L.; Huang, H.-M. Chem. Rev. 2015, 115, 3468.
(b) Huang, Z.; Lim, H. N.; Mo, F.; Young, M. C.; Dong, G. Chem. Soc. Rev. 2015, 44, 7764.
(c) Yang, Q.; Wang, Q.; Yu, Z. Chem. Soc. Rev. 2015, 44, 2305.
(d) Gensch, T.; Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev. 2016, 45, 2900.
[2] (a) Seregin, I. V.; Gevorgyan, V. Chem. Soc. Rev. 2007, 36, 1173.
(b) Wang, D.; Yu, X.; Ge, B.; Miao, H.; Ding, Y. Chin. J. Org. Chem. 2015, 35, 676 (in Chinese).(王大伟, 余晓丽, 葛冰洋, 苗红艳, 丁玉强, 有机化学, 2015, 35, 676).
(c) Hu, X.; Yang, B.; Yao, W.; Wang, D. Chin. J. Org. Chem. 2018, 38, 3296 (in Chinese).(胡昕宇, 杨伯斌, 姚玮, 王大伟, 有机化学, 2018, 38, 3296.)
(d) Wang, D.; Yu, X.; Yao, W.; Hu, W.; Ge, C. Chem. Eur. J. 2016, 22, 5543.
(e) Yu, X.; Wang, D.-S.; Xu, Z.; Yang, B.;Wang, D. Org. Chem. Front. 2017, 4, 1011.
(f) Wang, D.; Yu, X.; Xu, X.; Ge, B.; Wang, X.; Zhang, Y. Chem. Eur. J. 2016, 22, 8663.
[3] (a) Wang, D.; Zhao, K.; Xu, C.; Miao, H.; Ding, Y. ACS Catal. 2014, 4, 3910.
(b) Xu, Z.; Wang, D.-S.; Yu, X.; Yang, Y.; Wang, D. Adv. Synth. Catal. 2017, 359, 3332.
(c) Ye, D.; Huang, R.; Zhu, H.; Zou, L.-H.; Wang, D. Org. Chem. Front. 2019, 6, 62.
(d) Ge, C.; Sang, X.; Yao, W.; Zhang, L.; Wang, D. Green Chem. 2018, 20, 1805.
(e) Wu, Q.; Pan, L.; Du, G.; Zhang, C.;Wang, D. Org. Chem. Front. 2018, 5, 2668.
(f) Hu, X.; Zhu, H.; Sang, X.; Wang, D. Adv. Synth. Catal. 2018, 360, 4293.
(g) Xu, Z.; Yu, X.; Sang, X.; Wang, D. Green Chem. 2018, 20, 2571.
[4] (a) Uyanik, M.; Okamoto, H.; Yasui, T.; Ishihara, K. Science 2010, 328, 1376.
(b)Yan, Y.; Xu, K.; Fang, Y.; Wang, Z.-Y. J. Org. Chem. 2011, 76, 6849.
(c) Wang, D.; Ge, B.; Li, L.; Shan, J.; Ding, Y. J. Org. Chem. 2014, 79, 8607.
[5] Zhang, Z.; Liu, Q. Prog. Chem. 2006, 18, 270 (in Chinese).(张占辉, 刘庆彬, 化学进展, 2006, 18, 270.)
[6] (a) Von Der Heiden, D.; Bozkus, S.; Klussmann, M.; Breugst, M. J. Org. Chem. 2017, 82, 4037.
(b) Hao, W.-J.; Wang, S.-Y.; Ji, S.-J. ACS Catal. 2013, 3, 2501.
[7] Yasui, K.; Kato, T.; Kojima, K.; Nagasawa, K. Chem. Commun. 2015, 51, 2290.
[8] Uyanik, M.; Suzuki, D.; Yasui, T.; Ishihara, K. Angew. Chem., Int. Ed. 2011, 50, 5331.
[9] Varszegi, C.; Ernst, M.; Van Laar, F.; Sels, B. F.; Schwab, E.; De Vos, D. E. Angew. Chem., Int. Ed. 2008, 47, 1477.
[10] Siddaraju, Y.; Prabhu, K. R. J. Org. Chem. 2017, 82, 3084.
[11] Wu, W.; An, Y.; Li, J.; Yang, S.; Zhu, Z.; Jiang, H. Org. Chem. Front. 2017, 4, 1751.
[12] Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841.
[13] Yan, Y.; Zhang, Y.; Feng, C.; Zha, Z.; Wang, Z. Angew. Chem., Int. Ed. 2012, 51, 8077.
[14] Lamani, M.; Prabhu, K. R. J. Org. Chem. 2011, 76, 7938.
[15] Fei, Z.; Zhu, Y.-P.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X. Tetrahedron Lett. 2013, 54, 1222.
[16] Harrison, T. S.; Keating, G. M. CNS Drugs 2005, 19, 65.
[17] Yan, Y.; Xu, Y.; Niu, B.; Xie, H.-F.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
[18] Mohammed, S.; Vishwakarma, R. A.; Bharate, S. B. J. Org. Chem. 2015, 80, 6915.
[19] Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
[20] Beukeaw, D.; Udomsasporn, K.; Yotphan, S. J. Org. Chem. 2015, 80, 3447.
[21] Yang, L.; Shi, X.; Hu, B.-Q.; Wang, L.-X. Asian J. Org. Chem. 2016, 5, 494.
[22] (a) Khan, I.; Ibrar, A.; Ahmed, W.; Saeed, A. Eur. J. Med. Chem. 2015, 90, 124;
(b) He, L.; Li, H.; Chen, J.; Wu, X.-F. RSC Adv. 2014, 4, 12065;
(c) Connolly, D. J.; Cusack, D.; O'sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153.
[23] Nguyen, T. B.; Ermolenko, L.; Retailleau, P.; Al-Mourabit, A. Org. Lett. 2016, 18, 2177.
[24] Xiong, M.; Gao, Z.; Liang, X.; Cai, P.; Zhu, H.; Pan, Y. Chem. Commun. 2018, 54, 9679.
[25] Chen, Z.; Li, H.; Dong, W.; Miao, M.; Ren, H. Org. Lett. 2016, 18, 1334.
[26] Yang, Z.-Y.; Tian, T.; Du, Y.-F.; Li, S. Y.; Chu, C.-C.; Chen, L.-Y.; Li, D.; Liu, J.-Y.; Wang, B. Chem. Commun. 2017, 53, 8050.
[27] (a) Crich, D.; Banerjee, A. Acc. Chem. Res. 2007, 40, 151.
(b) Ruiz-Sanchis, P.; Savina, S. A.; Albericio, F.; Alvarez, M. Chem. Eur. J. 2011, 17, 1388.
[28] Baig, M. F.; Shaik, S. P.; Nayak, V. L.; Alarifi, A.; Kamal, A. Bioorg. Med. Chem. Lett. 2017, 27, 4039.
[29] Yi, X.; Xi, C. Tetrahedron 2017, 73, 1311.
[30] Gupta, A.; Deshmukh, M. S.; Jain, N. J. Org. Chem. 2017, 82, 4784.
[31] Hussain, S.; Parveen, S.; Hao, X.; Zhang, S.; Wang, W.; Qin, X.; Yang, Y.; Chen, X.; Zhu, S.; Zhu, C.; Ma, B. Eur. J. Med. Chem. 2014, 80, 383.
[32] Zhu, D.; Luo, W.-K.; Yang, L.; Ma, D.-Y. Org. Biomol. Chem. 2017, 15, 7112.
[33] Chen, K.; Gao, B.; Shang, Y.; Du, J.; Gu, Q.; Wang, J. Org. Biomol. Chem. 2017, 15, 8770.
[34] Gao, W.-C.; Zhao, J.-J.; Chang, H.-H.; Li, X.; Liu, Q.; Wei, W.-L. RSC Adv. 2014, 4, 49329.
[35] Zhao, X.; Zhang, L.; Li, T.; Liu, G.; Wang, H.; Lu, K. Chem. Commun. 2014, 50, 13121.
[36] Xiao, F.; Chen, H.; Xie, H.; Chen, S.; Yang, L.; Deng, G.-J. Org. Lett. 2014, 16, 50.
[37] Xiao, F.; Xie, H.; Liu, S.; Deng, G.-J. Adv. Synth. Catal. 2014, 356, 364.
[38] Kang, X.; Yan, R.; Yu, G.; Pang, X.; Liu, X.; Li, X.; Xiang, L.; Huang, G. J. Org. Chem. 2014, 79, 10605.
[39] Cao, H.; Yuan, J.; Liu, C.; Hu, X.; Lei, A. RSC Adv. 2015, 5, 41493.
[40] (a) Jereb, M.; Togni, A. Org. Lett. 2005, 7, 4041.
(b) Wang, W.; Li, H.; Wang, J.; Liao, L. Tetrahedron Lett. 2004, 45, 8229.
[41] Siddaraju, Y.; Prabhu, K. R. J. Org. Chem. 2016, 81, 7838.
[42] Pang, X.; Xiang, L.; Yang, X.; Yan, R. Adv. Synth. Catal. 2016, 358, 321.
[43] Yang, D.; Sun, P.; Wei, W.; Meng, L.; He, L.; Fang, B.; Jiang, W.; Wang, H. Org. Chem. Front. 2016, 3, 1457.
[44] Wu, S.-S.; Feng, C.-T.; Hu, D.; Huang, Y.-K.; Li, Z.; Luo, Z.-G.; Ma, S.-T. Org. Biomol. Chem. 2017, 15, 1680.
[45] Yu, H; Pi. C.; Wang, Y.; Cui, X.; Wu, Y. Chin. J. Org. Chem. 2018, 38, 124 (in Chinese).(余海洋, 皮超, 王勇, 崔秀灵, 吴养洁, 有机化学, 2018, 38, 124.)
[46] Vuppalapati, S. V. N.; Lee, Y. R. Tetrahedron 2012, 68, 8286.
[47] (a) Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748.
(b) Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2003, 2209.
[48] Zhu, Y.-P.; Liu, M.-C.; Jia, F.-C.; Yuan, J.-J.; Gao, Q.-H.; Lian, M.;Wu, A.-X. Org. Lett. 2012, 14, 3392.
[49] Nobuta, T.; Tada, N.; Fujiya, A.; Kariya, A.; Miura, T.; Itoh, A. Org. Lett. 2013, 15, 574.
[50] Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092.
[51] Raghavender Reddy, M.; Nageswara Rao, N.; Ramakrishna, K.; Meshram, H. M. Tetrahedron Lett. 2014, 55, 1898.
[52] Gao, Y.; Song, Q.; Cheng, G.; Cui, X. Org. Biomol. Chem. 2014, 12, 1044.
[53] Huang, H.-Y.; Wu, H.-R.; Wei, F.; Wang, D.; Liu, L. Org. Lett. 2015, 17, 3702.
[54] Zhang, Z.; Pi, C.; Tong, H.; Cui, X.; Wu, Y. Org. Lett. 2017, 19, 440.
[55] Wu, J.; Cui, X.; Chen, L.; Jiang, G.;Wu, Y. J. Am. Chem. Soc. 2009, 131, 13888.
[56] Liu, B.; Cheng, J.; Li, Y.; Li, J.-H. Chem. Commun. 2019, 55, 667.
[57] Yang, F.; Wang, F.; Wang, T.; Wang, Y.; Tian, S. Chem. Commun. 2014, 50, 2111.
[58] Choudhuri, K.; Achar, T. K.; Mal, P. Adv. Synth. Catal. 2017, 359, 3566.
[59] Xue, W.-J.; Zheng, K.-L.; Li, H.-Z.; Gao, F.-F.; Wu, A.-X. Tetrahedron Lett. 2014, 55, 4212.
[60] Samanta, S.; Donthiri, R. R.; Dinda, M.; Adimurthy, S. RSC Adv. 2015, 5, 66718.
[61] Liang, Y.; Wu, K.; Song, S.; Li, X.; Huang, X.; Jiao, N. Org. Lett. 2015, 17, 876.
[62] Wu, Y.-H.; Wu, Q.-L.; Wang, W.-P.; Wang, X.-C.; Quan, Z.-J. Adv. Synth. Catal. 2018, 360, 2382.
[63] Bao, Y.; Yang, X.; Zhou, Q.; Yang, F. Org. Lett. 2018, 20, 1966.
[64] Du, S.; Pi. C.; Wan, T.; Wu, Y.; Cui, X. Adv. Synth. Catal. 2019, 361, 1766.
[65] Jiang, H.; Huang, H.; Cao, H.; Qi, C. Org. Lett. 2010, 12, 5561.
[66] (a) Jin, Z. Nat. Prod. Rep. 2006, 23, 464.
(b) Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126.
(c) Wipf, P. Chem. Rev. 1995, 95, 2115.
[67] Xu, W.; Kloeckner, U.; Nachtsheim, B. J. J. Org. Chem. 2013, 78, 6065.
[68] Gao, Q.-H.; Fei, Z.; Zhu, Y.-P.; Lian, M.; Jia, F.-C.; Liu, M.-C.; She, N.-F.;Wu, A.-X. Tetrahedron 2013, 69, 22.
[69] Wu, X.; Gao, Q.; Liu, S.; Wu, A. Org. Lett. 2014, 16, 2888.
[70] Du, B.; Sun, P.-P. Sci. China Chem. 2014, 57, 1176.
[71] Rajeshkumar, V.; Chandrasekar, S.; Sekar, G. Org. Biomol. Chem. 2014, 12, 8512.
[72] (a) Millemaggi, A.; Taylor, R. J. K. Eur. J. Org. Chem. 2010, 2010, 4527.
(b) Silva, J. F. M. D.; Garden, S. J.; Pinto, A. C. J. Braz. Chem. Soc. 2001, 12, 273.
(c) Sumpter, W. C. Chem. Rev. 1944, 34, 393.
[73] Mupparapu, N.; Vishwakarma, R. A.; Ahmed, Q. N. Tetrahedron 2015, 71, 3417.
[74] (a) Kim, Y. H.; Kim, S. H. Tetrahedron Lett. 1995, 36, 6895.
(b) Pansare, S. V.; Gnana Ravi, R. Tetrahedron Lett. 1995, 36, 5959.
(c) Sai, K. K.; Esteves, P. M.; Da Penha, E. T.; Klumpp, D. A. J. Org. Chem. 2008, 73, 6506.
[75] Nachtsheim, B.; Finkbeiner, P. Synthesis 2013, 45, 979.
[76] Luo, W.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18, 2036.
[77] Wang, H.-X.; Wei, T.-Q.; Xu, P.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2018, 83, 13491.
[78] Zhu, Y.-P.; Lian, M.; Jia, F.-C.; Liu, M.-C.; Yuan, J.-J.; Gao, Q.-H.;Wu, A.-X. Chem. Commun. 2012, 48, 9086.
[79] Li, H.-Z.; Xue, W.-J.; Wu, A.-X. Tetrahedron 2014, 70, 4645.
[80] Geng, X.; Wu, X.; Wang, C.; Zhao, P.; Zhou, Y.; Sun, X.; Wang, L. J.; Guan, W. J.; Wu, Y. D.; Wu, A. X. Chem. Commun. 2018, 54, 12730.
[81] Sun, J.; Qiu, J.-K.; Zhu, Y.-L.; Guo, C.; Hao, W.-J.; Jiang, B.; Tu, S.-J. J. Org. Chem. 2015, 80, 8217.
[82] Sun, P.; Yang, D.; Wei, W.; Sun, X.; Zhang, W.; Zhang, H.; Wang, Y.; Wang, H. Tetrahedron 2017, 73, 2022.
[83] Xu, Y.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2017, 82, 9637.
[84] Zhao, J.; Huang, H.; Wu, W.; Chen, H.; Jiang, H. Org. Lett. 2013, 15, 2604.
[85] Kumar, A.; Gupta, L. P.; Kumar, M. RSC Adv. 2013, 3, 18771.
[86] Zhang, Z.; Xie, C.; Tan, X.; Song, G.; Wen, L.; Gao, H.; Ma, C. Org. Chem. Front. 2015, 2, 942.
[87] Reddy, N. N. K.; Mohan, D. C.; Adimurthy, S. Tetrahedron Lett. 2016, 57, 1074.
[88] (a) Henry, J. B.; Macdonald, R. J.; Gibbad, H. S.; Mcnab, H.; Mount, A. R. Phys. Chem. Chem. Phys. 2011, 13, 5235.
(b) Liu, B.; Wang, Z.; Wu, N.; Li, M.; You, J.; Lan, J. Chem. Eur. J. 2012, 18, 1599.
[89] (a) Michael, J. P. Nat. Prod. Rep. 2008, 25, 139.
(b) Hazra, A.; Mondal, S.; Maity, A.; Naskar, S.; Saha, P.; Paira, R.; Sahu, K. B.; Paira, P.; Ghosh, S.; Sinha, C.; Samanta, A.; Banerjee, S.; Mondal, N. B. Eur. J. Med. Chem. 2011, 46, 2132.
(c) Wang, H.; Guo, S.; Qian, D.; Qian, Y.; Duan, J. A. J. Pharm. Biomed. Anal. 2012, 67~68, 16.
[90] Mani, G. S.; Shaik, S. P.; Tangella, Y.; Bale, S.; Godugu, C.; Kamal, A. Org. Biomol. Chem. 2017, 15, 6780.
[91] Gao, Q.; Liu, Z.; Wang, Y.; Wu, X.; Zhang, J.; Wu, A. Adv. Synth. Catal. 2018, 360, 1364.
[92] Gao, Q.; Wang, Y.; Wang, Q.; Zhu, Y.; Liu, Z.; Zhang, J. Org. Biomol. Chem. 2018, 16, 9030.
/
| 〈 |
|
〉 |
