分子碘催化氧化C(sp3)—H功能化反应的研究进展
收稿日期: 2020-08-15
修回日期: 2020-10-22
网络出版日期: 2020-11-19
基金资助
中国科技部“重大新药创制课题”(2018ZX09J18108-004-001); 陕西省重点研发计划(2019ZDLSF03-03)
Research Progress in C(sp3)—H Functionalization Reaction via Molecular Iodine-Catalyzed Oxidation
Received date: 2020-08-15
Revised date: 2020-10-22
Online published: 2020-11-19
Supported by
National Science and Technology Major Project of China on “Key New Drug Creation and Development Program”(2018ZX09J18108-004-001); Shaanxi Province Key Research and Development Program(2019ZDLSF03-03)
现代有机合成中, C—H功能化反应可以用于直接构建各种生物活性骨架以及增加目标分子结构的复杂性, 是对传统合成方法的有效补充, 其中惰性C(sp3)—H功能化长期以来是该领域的难点. 目前, 碘试剂已被确定为经济和生态上无害的过渡金属替代品, 在具有挑战性的C(sp3)—H功能化反应中已经取得了卓有成效的进展. 分子碘与高价芳基碘试剂、二甲基亚砜(DMSO)、过氧化物以及氧气等组合, 能够高效地催化不同反应类型的C(sp3)—H功能化反应, 在不同氧化体系下具有不同的反应特点和机制. 另外, 近年来, 过渡金属/分子碘协同催化以及含碘电化学催化等新型碘催化体系在C(sp3)—H功能化反应中也得到了前所未有的发展. 综述了2015年至今分子碘在不同氧化体系下催化的C(sp3)—H功能化反应, 希望能进一步了解分子碘的绿色催化体系, 为深入研究C(sp3)—H功能化反应提供帮助.
关键词： 分子碘; C(sp3)—H功能化; 氧化体系; 绿色化学; 电化学
张露文 , 何炜 . 分子碘催化氧化C(sp3)—H功能化反应的研究进展[J]. 有机化学, 2021 , 41(4) : 1359 -1395 . DOI: 10.6023/cjoc202008027
In modern organic synthesis, C—H functionalization can be used to construct various bioactive skeletons quickly and directly, and increase the complexity of the target molecular structure, which becomes an effective supplement to the traditional methods. Among them, C(sp3)—H functionalization has long been a big challenge in this field. Molecular iodine has been identified as an economically and ecologically harmless transition metal substitute, and tremendous progress has been made in the challenging C(sp3)—H functionalization reaction recently. The molecular iodine-catalyzed C(sp3)—H functionalization reactions under different oxidation systems have different reaction characteristics and mechanisms. The combination of molecular iodine and hypervalent aryl iodanes, dimethyl sulfoxide (DMSO), peroxide and oxygen can efficiently catalyze the functionalization of C(sp3)—H with different mechanisms. Recently, transition-metal/iodine co-cataly- sis and iodine-containing electrochemical catalysis have also made unprecedented progress in C(sp3)—H functionalization reaction. Herein, the progress of C(sp3)—H functionalization catalyzed by iodine under different oxidation systems from 2015 to now is summarized. The research on the green catalytic system of molecular iodine in the C(sp3)—H functionalization reaction is summarized and prospected.
| [1] | Togo, H.; Iida, S. Synlett 2006, 2006,2159. |
| [2] | Ren, Y.M.; Cai, C.; Yang, R.C. RSC Adv. 2013, 3,7182. |
| [3] | Chu, C.M.; Gao, S.J.; Sastry, M.N. V.; Yao, C.F. Tetrahedron Lett. 2005, 46,4971. |
| [4] | Yin, G.D.; Fan, L.; Ren, T.B.; Zheng, C.Y.; Tao, Q.; Wu, A.X.; She, N.F. Org. Biomol. Chem. 2012, 10,8877. |
| [5] | Wang, S.Y.; Ji, S.J.; Loh, T.P. Synlett 2003, 2003,2377. |
| [6] | Parvatkar, P.T.; Manetsch, R.; Banik, B.K. Chem.-Asian J. 2019, 14,6. |
| [7] | Mphahlele, M.J. Molecules 2009, 14,5308. |
| [8] | Gaikwad, S.; Kamble, D.; Lokhande, P. Tetrahedron Lett. 2018, 59,2387. |
| [9] | Humne, V.; Dangat, Y.; Vanka, K.; Lokhande, P. Org. Biomol. Chem. 2014, 12,4832. |
| [10] | Stateman, L.M.; Nakafuku, K.M.; Nagib, D.A. Synthesis 2018, 50,1569. |
| [11] | Zhao, Y.Y.; Wang, E.B.; Wang, Y.L. Chin. J. Org. Chem. 2017, 37,866. (in Chinese) |
| [11] | ( 赵玉英, 王二兵, 王颖莉, 有机化学, 2017, 37,866.) |
| [12] | Shi, Z.J.; Wang, L.H.; Cui, X.L. Chin. J. Org. Chem. 2019, 39,1596. (in Chinese) |
| [12] | ( 施兆江, 王连会, 崔秀灵, 有机化学, 2019, 39,1596.) |
| [13] | Xu, X.M.; Chen, D.M.; Wang, Z.L. Chin. J. Org. Chem. 2019, 39,3338. (in Chinese) |
| [13] | ( 徐鑫明, 陈德茂, 王祖利, 有机化学, 2019, 39,3338.) |
| [14] | Du, X.P.; Zhang, X.; Hou, F.; Liu, X.J.; Wang, X.C.; Quan, Z.J. Chin. J. Org. Chem. 2020, 40,1337. (in Chinese) |
| [14] | ( 杜兴鹏, 张玺, 候飞, 刘小军, 王喜存, 权正军, 有机化学, 2020, 40,1337.) |
| [15] | Yang, L.F.; Hui, R.J.; Shan, H.Y.; Gong, K. Chin. J. Org. Chem. 2017, 37,3242. (in Chinese) |
| [15] | ( 杨丽烽, 惠人杰, 单恒悦, 巩凯, 有机化学, 2017, 37,3242.) |
| [16] | Blanksby, S.J.; Ellison, G.B. Acc. Chem. Res. 2003, 36,255. |
| [17] | Sim?es, J.A. M.; Beauchamp, J.L. Chem. Rev. 1990, 90,629. |
| [18] | Siegbahn, P.E. M. J. Phys. Chem. 1995, 99,12723. |
| [19] | Yeung, C.S.; Dong, V.M. Chem. Rev. 2011, 111,1215. |
| [20] | Beccalli, E.M.; Broggini, G.; Martinelli, M.; Sottocornola, S. Chem. Rev. 2007, 107,5318. |
| [21] | Hosseinian, A.; Ahmadi, S.; Nasab, F.A. H.; Mohammadi, R.; Vessally, E. Top. Curr. Chem. 2018, 376,1. |
| [22] | Li, C.J.; Li, Z.P. Pure Appl. Chem. 2006, 78,935. |
| [23] | Borpatra, P.J.; Deka, B.; Deb, M.L.; Baruah, P.K. Org. Chem. Front. 2019, 6,3445. |
| [24] | Chu, J.C. K.; Rovis, T. Angew. Chem., Int. Ed. 2017, 56,2. |
| [25] | Meng, G.Y.; Guo, T.J.; Ma, T.C.; Zhang, J.; Shen, Y.C.; Sharpless, K.B.; Dong, J.J. Nature 2019, 574,86. |
| [26] | Wu, X.; Gao, Q.H.; Geng, X.; Zhang, J.J.; Wu, Y.D.; Wu, A.X. Org. Lett. 2016, 18,2507. |
| [27] | Stateman, L.M.; Wappes, E.A.; Nakafuku, K.M.; Edwards, K.M.; Nagib, D.A. Chem. Sci. 2019, 10,2693. |
| [28] | Long, J.G.; Cao, X.; Zhu, L.Z.; Qiu, R.H.; Au, C.T.; Yin, S.F.; Iwasaki, T.; Kambe, N. Org. Lett. 2017, 19,2793. |
| [29] | Siddaraju, Y.; Prabhu, K.R. Org. Lett. 2016, 18,6090. |
| [30] | Liang, Y.F.; Li, X.Y.; Wang, X.Y.; Zou, M.C.; Tang, C.H.; Liang, Y.J.; Song, S.; Jiao, N. J. Am. Chem. Soc. 2016, 138,12271. |
| [31] | Reddy, P.N.; Reddy, B.V. S.; Padmaja, P. Curr. Org. Synth. 2018, 15,815. |
| [32] | Monga, A.; Bagchi, S.; Sharma, A. New J. Chem. 2018, 42,1551. |
| [33] | Tashrifi, Z.; Khanaposhtani, M.M.; Larijani, B.; Mahdavi, M. Adv. Synth. Catal. 2020, 362,65. |
| [34] | Sudo, Y.; Yamaguchi, E.; Itoh, A. Org. Lett. 2017, 19,1610. |
| [35] | Rong, H.J.; Yao, J.J.; Li, J.K.; Qu, J. J. Org. Chem. 2017, 82,5557. |
| [36] | Huang, H.Y.; Wu, H.R.; Wei, F.; Wang, D.; Liu, L. Org. Lett. 2015, 17,3702. |
| [37] | Qian, P.; Zha, Z.G.; Wang, Z.Y. ChemElectroChem 2020, 12,2527. |
| [38] | Yang, L.; Xu, G.H.; Ma, J.J.; Yang, Q.; Feng, A.; Cui, J.G. Chin. J. Org. Chem. 2020, 40,28. (in Chinese) |
| [38] | ( 杨柳, 许国贺, 马晶军, 杨倩, 冯安, 崔景港, 有机化学, 2020, 40,28.) |
| [39] | Hofmann, A.W. Chem. Ber. 1883, 16,558. |
| [40] | Armas, P.D.; Carrau, R.; Concepción, J.I.; Francisco, C.G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26,2493. |
| [41] | Dorta, R.L.; Francisco, C.G.; Suárez, E. J. Chem. Soc., hem. Commun. 1989,1168. |
| [42] | Francisco, C.G.; Herrera, A.J.; Kennedy, A.R.; Melián, D.; Suárez, E. Angew. Chem., Int. Ed. 2002, 41,856. |
| [43] | Paz, N.R.; Rodríguez-Sosa, D.; Valdés, H.; Marticorena, R.; Melián, D.; Copano, M.B.; González, C.C.; Herrera, A.J. Org. Lett. 2015, 17,2370. |
| [44] | Martínez, C.; Mu?iz, K. Angew. Chem., Int. Ed. 2015, 54,8287. |
| [45] | Castillo, E.D.; Mu?iz, K. Org. Lett. 2019, 21,705. |
| [46] | Barluenga, J.; González, J.M.; Campos, P.J.; Asensio, G. Angew. Chem., Int. Ed. 1985, 24,319. |
| [47] | Zhdankin, V.V.; Koposov, A.Y.; Yashin, N.V. Tetrahedron Lett. 2002, 43,5735. |
| [48] | Carlsson, A.C. C.; Mehmeti, K.; Uhrbom, M.; Karim, A.; Bedin, M.; Puttreddy, R.; Kleinmaier, R.; Neverov, A.A.; Nekoueishahraki, B.; Gr?fenstein, J.; Rissanen, K.; Erdélyi, M. J. Am. Chem. Soc. 2016, 138,9853. |
| [49] | Duhamel, T.; Martínez, M.D.; Sideri, I.K.; Mu?iz, K. ACS Catal. 2019, 9,7741. |
| [50] | Bosnidou, A.E.; Duhamel, T.; Mu?iz, K. Eur. J. Org. Chem. 2020, 2020,6361. |
| [51] | Bosnidou, A.E.; Mu?iz, K. Angew. Chem., Int. Ed. 2019, 58,7485. |
| [52] | Zhang, D.; Wang, H.; Cheng, H.C.; Hernández, J.G.; Bolm, C. Adv. Synth. Catal. 2017, 359,4274. |
| [53] | Genovino, J.; Lütz, S.; Sames, D.; Touré, B.B. J. Am. Chem. Soc. 2013, 135,12346. |
| [54] | Ripper, J.A.; Tiekink, E.R. T.; Scammells, P.J. Bioorg. Med. Chem. Lett. 2001, 11,443. 4ea89b7f-29df-4105-8bdc-665e2f95ef6e |
| [55] | Lancefield, C.S.; Zhou, L.; Lébl, T.; Slawin, A.M. Z.; Westwood, N.J. Org. Lett. 2012, 14,6166. |
| [56] | Shu, X.Z.; Xia, X.F.; Yang, Y.F.; Ji, K.G.; Liu, X.Y.; Liang, Y.M. J. Org. Chem. 2009, 74,7464. |
| [57] | Zhu, Y.; Shao, L.D.; Deng, Z.T.; Bao, Y.; Shi, X.; Zhao, Q.S. J. Org. Chem. 2018, 83,10166. |
| [58] | Kanyiva, K.S.; Tane, M.; Shibata, T. J. Org. Chem. 2019, 84,12773. |
| [59] | Wappes, E.A.; Nakafuku, K.M.; Nagib, D.A. J. Am. Chem. Soc. 2017, 139,10204. |
| [60] | Prusinowski, A.F.; Twumasi, R.K.; Wappes, E.A.; Nagib, D.A. J. Am. Chem. Soc. 2020, 142,5429. |
| [61] | Zhao, P.; Wu, X.; Geng, X.; Wang, C.; Zhou, Y.; Wu, Y.D.; Wu, A.X. J. Org. Chem. 2019, 84,8322. |
| [62] | Monga, A.; Bagchi, S.; Sharma, A. New J. Chem. 2018, 42,1551. |
| [63] | Gao, Q.H.; Liu, S.; Wu, X.; Zhang, J.J.; Wu, A.X. J. Org. Chem. 2015, 80,5984. |
| [64] | Gao, Q.H.; Liu, S.; Wu, X.; Wu, A.X. Org. Lett. 2014, 16,4582. |
| [65] | Wu, X.; Geng, X.; Zhao, P.; Zhang, J.J.; Wu, Y.D.; Wu, A.X. Chem. Commun. 2017, 53,3438. |
| [66] | Wu, X.; Geng, X.; Zhao, P.; Zhang, J.J.; Gong, X.X.; Wu, Y.D.; Wu, A.X. Org. Lett. 2017, 19,1550. |
| [67] | Wu, X.; Zhao, P.; Geng, X.; Zhang, J.J.; Gong, X.X.; Wu, Y.D.; Wu, A.X. Org. Lett. 2017, 19,3319. |
| [68] | Wu, X.; Geng, X.; Zhao, P.; Wu, Y.D.; Wu, A.X. Org. Lett. 2017, 19,4584. |
| [69] | Xue, W.J.; Gao, Q.H.; Wu, A.X. Tetrahedron Lett. 2015, 56,7115. |
| [70] | Liu, S.; Xi, H.L.; Zhang, J.J.; Wu, X.; Gao, Q.H.; Wu, A.X. Org. Biomol. Chem. 2015, 13,8807. |
| [71] | Wu, X.; Gao, Q.H.; Geng, X.; Zhang, J.J.; Wu, Y.D.; Wu, A.X. Org. Lett. 2016, 18,2507. |
| [72] | Qun, C.; Zhuang, S.Y.; Yang, M.; Peng, N.; Liu, Y.; Wu, A.X. Tetrahedron 2019, 75,130756. |
| [73] | Wang, C.; Geng, X.; Zhao, P.; Zhou, Y.; Wu, Y.D.; Wu, A.X. Org. Chem. Front. 2019, 6,2534. |
| [74] | Weng, W.Z.; Gao, Y.H.; Zhang, X.; Liu, Y.H.; Shen, Y.J.; Zhu, Y.P.; Sun, Y.Y.; Meng, Q.G.; Wu, A.X. Org. Biomol. Chem. 2019, 17,2087. |
| [75] | Zhang, Z.Y.; Xie, C.X.; Tan, X.C.; Song, G.L.; Wen, L.L.; Gao, H.; Ma, C. Org. Chem. Front. 2015, 2,942. |
| [76] | Xie, C.X.; Zhang, Z.Y.; Yang, B.C.; Song, G.L.; Gao, H.; Wen, L.L.; Ma, C. Tetrahedron 2015, 71,1831. |
| [77] | Satish, G.; Polu, A.; Ramar, T.; Ilangovan, A. J. Org. Chem. 2015, 80,5167. |
| [78] | Liang, Y.F.; Wu, K.; Song, S.; Li, X.Y.; Huang, X.Q.; Jiao, N. Org. Lett. 2015, 17,876. |
| [79] | Liang, Y.F.; Li, X.Y.; Wang, X.Y.; Zou, M.C.; Tang, C.H.; Liang, Y.J.; Song, S.; Jiao, N. J. Am. Chem. Soc. 2016, 138,12271. |
| [80] | Liang, Y.F.; Song, S.; Ai, L.S.; Li, X.W.; Jiao, N. Green Chem. 2016, 18,6462. |
| [81] | Mupparapu, N.; Vishwakarma, R.A.; Ahmed, Q.N. Tetrahedron 2015, 71,3417. |
| [82] | Yang, L.; Shi, X.; Hu, B.Q.; Wang, L.X. Asian J. Org. Chem. 2016, 5,494. |
| [83] | Sun, P.F.; Yang, D.S.; Wei, W.; Sun, X.J.; Zhang, W.H.; Zhang, H.; Wang, Y.; Wang, H. Tetrahedron 2017, 73,2022. |
| [84] | Siddaraju, Y.; Prabhu, K.R. Org. Lett. 2016, 18,6090. |
| [85] | Siddaraju, Y.; Prabhu, K.R. Org. Biomol. Chem. 2017, 15,5191. |
| [86] | Chen, S.H.; Li, Y.; Chen, J.Y.; Xu, X.H.; Su, L.B.; Tang, Z.; Au, C.T.; Qiu, R.H. Synlett 2016, 27,2339. |
| [87] | Xi, L.Y.; Zhang, R.Y.; Shi, L.; Chen, S.Y.; Yu, X.Q. Beilstein J. Org. Chem. 2016, 12,1072. |
| [88] | Xiong, M.T.; Gao, Z.; Liang, X.; Cai, P.F.; Zhu, H.P.; Pan, Y.J. Chem. Commun. 2018, 54,9679. |
| [89] | Barak, D.S.; Dighe, S.U.; Avasthi, I.; Batra, S. J. Org. Chem. 2018, 83,3537. |
| [90] | Rahim, A.; Shaik, S.P.; Baig, M.F.; Alarifi, A.; Kamal, A. Org. Biomol. Chem. 2018, 16,635. |
| [91] | Mani, G.S.; Donthiboina, K.; Shankaraiah, N.; Kamal, A. New J. Chem. 2019, 43,15999. |
| [92] | Salihila, J.; Silva, L.; Pulgar, H.P. D.; Molina, A.Q.; González-Coloma, A.; Olmeda, A.S.; Moral, J. F., Q.D.; Barrero, A.F. J. Org. Chem. 2019, 84,6886. |
| [93] | Chen, H.; Liu, L.; Huang, T.Z.; Chen, J.; Chen, T.Q. Adv. Synth. Catal. 2020, 362,3332. |
| [94] | Liu, M.; Chen, T.Q.; Zhou, Y.B.; Yin, S.F. Catal. Sci. Technol. 2016, 6,5792. |
| [95] | Liu, M.; Chen, X.; Chen, T.Q.; Xu, Q.; Yin, S.F. Org. Biomol. Chem. 2017, 15,9845. |
| [96] | Chen, H.; Liu, L.; Huang, T.Z.; Jing, C.; Chen, T.Q. Org. Biomol. Chem. 2020, 16,3332. |
| [97] | Cao, Y.; Liu, L.; Huang, T.; Chen, T.Q. New J. Chem. 2020, 44,8697. |
| [98] | Jayram, J.; Xulu, B.A.; Jeena, V. Tetrahedron 2019, 75,130617. |
| [99] | Shang, Z.H.; Sun, J.; Guo, J.S.; Sun, Y.Y.; Weng, W.Z.; Zhang, Z.X.; Li, Z.J.; Zhu, Y.P. Tetrahedron 2020, 76,130887. |
| [100] | Grigoropoulou, G.; Clark, J.H.; Elings, J.A. Green Chem. 2003, 5,1. |
| [101] | Faveri, G.D.; Ilyashenko, G.; Watkinson, M. Chem. Soc. Rev. 2011, 40,1722. |
| [102] | Tang, S.; Liu, K.; Long, Y.; Qi, X.T.; Lan, Y.; Lei, A.W. Chem. Commun. 2015, 51,8769. |
| [103] | Tang, S.; Liu, K.; Long, Y.; Gao, X.L.; Gao, M.; Lei, A.W. Org. Lett. 2015, 17,2404. |
| [104] | Cao, H.; Yuan, J.W.; Liu, C.; Hu, X.Q.; Lei, A.W. RSC Adv. 2015, 5,41493. |
| [105] | Samanta, S.; Donthiri, R.R.; Dindaa, M.; Adimurthy, S. RSC Adv. 2015, 5,66718. |
| [106] | Vadagaonkar, K.S.; Kalmode, H.P.; Murugan, K.; Chaskar, A.C. RSC Adv. 2015, 5,5580. |
| [107] | Vadagaonkar, K.S.; Kalmode, H.P.; Prakash, S.; Chaskar, A.C. Synlett 2015, 26,1677. |
| [108] | Verma, A.; Patel, S.; Meenakshi; Kumar, A.; Yadav, A.; Kumar, S.; Jana, S.; Sharma, S.; Prasad, C.D.; Kumar, S. Chem. Commun. 2015, 51,1371. |
| [109] | Luo, W.K.; Shi, X.; Zhou, W.; Yang, L. Org. Lett. 2016, 18,2036. |
| [110] | Shi, X.; Zhang, F.; Luo, W.K.; Yang, L. Synlett 2017, 28,494. |
| [111] | Luo, W.K.; Xu, C.L.; Yang, L. Tetrahedron Lett. 2019, 60,151328. |
| [112] | Shantharjun, B.; Rajeswari, R.; Vani, D.; Unnava, R.; Sridhar, B.; Reddy, K.R. Asian J. Org. Chem. 2019, 8,2162. |
| [113] | Zhu, D.; Luo, W.K.; Yang, L.; Ma, D.Y. Org. Biomol. Chem. 2017, 15,7112. |
| [114] | Chen, Z.K.; Li, H.L.; Dong, W.P.; Miao, M.Z.; Ren, H.J. Org. Lett. 2016, 18,1334. |
| [115] | Wei, W.; Cui, H.H.; Yang, D.S.; Liu, X.X.; He, C.L.; Dai, S.C.; Wang, H. Org. Chem. Front. 2017, 4,26. |
| [116] | Chen, K.L.; Gao, B.; Shang, Y.G.; Du, J.Y.; Gu, Q.L.; Wang, J.X. Org. Biomol. Chem. 2017, 15,8770. |
| [117] | Sun, K.; Lv, Y.H.; Chen, Y.H.; Zhou, T.T.; Xing, Y.Y.; Wang, X. Org. Biomol. Chem. 2017, 15,4464. |
| [118] | Deb, M.L.; Borpatra, P.J.; Saikia, P.J.; Baruah, P.K. Synlett 2017, 28,461. |
| [119] | Long, J.G.; Cao, X.; Zhu, L.Z.; Qiu, R.H.; Au, C.T.; Yin, S.F.; Iwasaki, T.; Kambe, N. Org. Lett. 2017, 19,2793. |
| [120] | Yaragorla, S.; Babu, V.P. Tetrahedron Lett. 2017, 58,1879. |
| [121] | Wang, J.; Zhang, F.D.; Tang, D.; Wu, P.; Zhang, X.G.; Chen, B.H. RSC Adv. 2017, 7,24594. |
| [122] | Wei, W.T.; Zhu, W.M.; Bao, W.H.; Chen, W.T.; Huang, Y.L.; Gao, L.H.; Xu, X.D.; Wang, Y.N.; Chen, G.P. ACS Sustainable Chem. Eng. 2018, 6,5615. |
| [123] | Chen, C.; Liu, W.B.; Zhou, P.; Liu, H.L. RSC Adv. 2017, 7,20394. |
| [124] | Duhamel, T.; Stein, C.J.; Martínez, C.; Reiher, M.; Mu?iz, K. ACS Catal. 2018, 8,3918. |
| [125] | Becker, P.; Duhamel, T.; Stein, C.J.; Reiher, M.; Mu?iz, K. Angew. Chem., Int. Ed. 2017, 56,8004. |
| [126] | Duhamel, T.; Mu?iz, K. Chem. Commun. 2019, 55,933. |
| [127] | Wang, H.X.; Wei, T.Q.; Xu, P.; Wang, S.Y.; Ji, S.J. J. Org. Chem. 2018, 83,13491. |
| [128] | Liu, L.; Tan, C.; Fan, R.; Wang, Z.H.; Du, H.G.; Xu, K.; Tan, J.J. Org. Biomol. Chem. 2019, 17,252. |
| [129] | Valeur, E.; Bradley, M. Chem. Soc. Rev. 2009, 38,606. |
| [130] | El-Faham, A.; Albericio, F. Chem. Rev. 2011, 111,6557. |
| [131] | Li, J.; Lear, M.J.; Kawamoto, Y.; Umemiya, S.; Wong, A.R.; Kwon, E.; Sato, I.; Hayashi, Y. Angew. Chem., Int. Ed. 2015, 127,13178. |
| [132] | Huang, H.Y.; Wu, H.R.; Wei, F.; Wang, D.; Liu, L. Org. Lett. 2015, 17,3702. |
| [133] | Nguyen, T.B.; Ermolenko, L.; Retailleau, P.; Al-Mourabit, A. Org. Lett. 2016, 18,2177. |
| [134] | Sudo, Y.; Yamaguchi, E.; Itoh, A. Org. Lett. 2017, 19,1610. |
| [135] | Yang, J.Y.; Xie, D.T.; Zhou, H.Y.; Chen, S.W.; Huo, C.D.; Li, Z. Org. Chem. Front. 2018, 5,1325. |
| [136] | Tuo, X.L.; Chen, S.P.; Jiang, P.Y.; Ni, P.H.; Wang, X.D.; Deng, G.J. RSC Adv. 2020, 10,8348. |
| [137] | Lv, Y.H.; Sun, K.; Wang, T.T.; Li, G.; Pu, W.Y.; Chai, N.N.; Shen, H.H.; Wu, Y.T. RSC Adv. 2015, 7,72142. |
| [138] | Lv, Y.H.; Sun, K.; Wang, T.T.; Wu, Y.T.; Li, G.; Pu, W.Y.; Mao, S.K. Asian J. Org. Chem. 2016, 5,325. |
| [139] | Lv, Y.H.; Pu, W.Y.; Niu, J.J.; Wang, Q.Q.; Chen, Q. Tetrahedron Lett. 2018, 59,1497. |
| [140] | Zhou, Y.; Chen, J.W.; Elsayed, A.A.; Zhang, Z.G.; Bao, Z.B.; Yang, Q.W.; Yang, Y.W.; Ren, Q.L. Catal. Lett. 2019, 149,574. |
| [141] | Sridhar, A.; Selvaraj, M. ChemistrySelect 2019, 4,1890. |
| [142] | Zhang, J.; Zhao, X.; Liu, P.; Sun, P.P. J. Org. Chem. 2019, 84,12596. |
| [143] | Tan, C.; Liu, Y.G.; Liu, X.Y.; Jia, H.X.; Xu, K.; Huang, S.H.; Wang, W.J.; Tan, J.J. Org. Chem. Front. 2020, 7,780. |
| [144] | Castanedo, G.; Liu, Y.Z.; Crawford, J.J.; Braun, M.G. J. Org. Chem. 2016, 81,8617. |
| [145] | Wang, P.; Gao, X.L.; Huang, P.F.; Lei, A.W. ChemCatChem 2020, 1,27. |
| [146] | Hu, X.; Nie, L.; Zhang, G.T.; Lei, A.W. Angew. Chem., Int. Ed. 2020, 59,15238. |
| [147] | Tang, S.; Wang, S.Y.; Liu, Y.C.; Cong, H.J.; Lei, A.W. Angew. Chem., Int. Ed. 2018, 57,4737. |
| [148] | Liu, K.; Song, C.L.; Wu, J.R.; Deng, Y.Q.; Tang, S.; Lei, A.W. Green Chem. 2019, 21,765. |
| [149] | Liang, S.; Zeng, C.C.; Tian, H.Y.; Sun, B.G.; Luo, X.G.; Ren, F.Z. J. Org. Chem. 2016, 81,11565. |
| [150] | Liang, S.; Zeng, C.C.; Tian, H.Y.; Sun, B.G.; Luo, X.G.; Ren, F.Z. Adv. Synth. Catal. 2018, 360,1444. |
| [151] | Qian, P.; Yan, Z.; Zhou, Z.H.; Hu, K.F.; Wang, J.W.; Li, Z.B.; Zha, Z.G.; Wang, Z.Y. Org. Lett. 2018, 20,6359. |
| [152] | Qian, P.; Zhou, Z.H.; Hu, K.F.; Wang, J.W.; Li, Z.B.; Zha, Z.G.; Wang, Z.Y. Org. Lett. 2019, 21,6403. |
| [153] | Wang, J.W.; Qian, P.; Hu, K.F.; Zha, Z.G.; Wang, Z.Y. ChemElectroChem 2019, 16,4292. |
| [154] | Rafiee, M.; Wang, F.; Hruszkewycz, D.P.; Stahl, S.S. J. Am. Chem. Soc. 2017, 140,22. |
| [155] | Wang, H.Q.; Zhang, J.J.; Tan, J.J.; Xin, L.L.; Li, Y.P.; Zhang, S.; Xu, K. Org. Lett. 2018, 20,2505. |
| [156] | Mohan, D.C.; Ravi, C.; Pappula, V.; Adimurthy, S. J. Org. Chem. 2015, 80,6846. |
| [157] | Zhao, Z.G.; Wang, T.; Yuan, L.; Ji, X.W.; Zhao, J.F. RSC Adv. 2015, 5,75386. |
| [158] | Gao, Q.H.; He, S.; Wu, X.; Zhang, J.J.; Bai, S.P.; Wu, Y.D.; Wu, A.X. Org. Chem. Front. 2018, 5,765. |
| [159] | Iwahama, T.; Syojyo, K.; Sakaguchi, S.; Ishii, Y. Org. Process Res. Dev. 1998, 2,255. |
| [160] | Wu, X.; Zhao, P.; Geng, X.; Wang, C.; Wu, Y.D.; Wu, A.X. Org. Lett. 2018, 20,688. |
| [161] | Geng, X.; Wang, C.; Huang, C.; Bao, Y.; Zhao, P.; Zhou, Y.; Wu, Y.D.; Feng, L.L.; Wu, A.X. Org. Lett. 2020, 22,140. |
| [162] | Wu, X.; Zhang, J.J.; Liu, S.; Gao, Q.H.; Wu, A.X. Adv. Synth. Catal. 2016, 358,218. |
| [163] | Yi, X.L.; Xi, C.J. Tetrahedron 2017, 73,1311. |
| [164] | Ujwaldev, S.M.; Rohit, K.R.; Harry, N.A.; Anilkumar, G. Tetrahedron Lett. 2019, 13,150950. |
| [165] | Sangeetha, S.; Sekar, G. Org. Lett. 2018, 21,75. |
| [166] | Sangeetha, S.; Sekar, G. Chem Commun. 2020, 56,10906. |
| [167] | Chen, L.S.; Zhang, L.B.; Tian, Y.; Li, J.H.; Liu, Y.Q. Eur. J. Org. Chem. 2020, 2020,5523. |
| [168] | Zhang, H.W.; Mu?iz, K. ACS Catal. 2017, 7,4122. |
| [169] | Yavari, I.; Hosseinpour, R.; Skoulika, S. Synlett 2015, 26,380. |
| [170] | Usami, K.; Nagasawa, Y.; Yamaguchi, E.; Tada, N.; Itoh, A. Org. Lett. 2016, 18,8. |
| [171] | Reddy, N.N. K.; Mohan, D.C.; Adimurthy, S. Tetrahedron Lett. 2016, 57,1074. |
| [172] | Pang, X.B.; Xiang, L.K.; Ma, J.X.; Yang, X.D.; Yan, R.L. RSC Adv. 2016, 6,111713. |
| [173] | Rong, H.J.; Yao, J.J.; Li, J.K.; Qu, J. J. Org. Chem. 2017, 82,5557. |
| [174] | Liu, R.H.; Wang, Y.K.; Weng, Y.M.; Yao, C.P.; Zhang, Y.; Zhu, G.Z.; He, X.A.; Xu, K.P.; Tan, G.S. Synlett 2017, 28,1083. |
| [175] | Liu, X.Z.; Zhou, Y.X.; Yang, Z.Q.; Li, Q.; Zhao, L.; Liu, P.J. J. Org. Chem. 2018, 83,4665. |
| [176] | Zhang, J.; Zheng, T.T.; Zhang, J.D. Eur. J. Org. Chem. 2020, 2020,860. |
/
| 〈 |
|
〉 |
