Progress in C—H Bond Functionalization on C-3 Position of Imidazo[1, 2-a] pyridines
- Corresponding author: Zhang Lianyang, zhlysheep@163.com
Citation:
Jin Cheng'an, Xu Qing, Feng Gaofeng, Jin Yang, Zhang Lianyang. Progress in C—H Bond Functionalization on C-3 Position of Imidazo[1, 2-a] pyridines[J]. Chinese Journal of Organic Chemistry,
;2018, 38(4): 775-790.
doi:
10.6023/cjoc201709044
Tresadern, G.; Cid, J. M.; Macdonald, G. J.; Vega, J. A.; de Lucas, A. I.; García, A.; Matesanz, E.; Linares, M. L.; Oehlrich, D.; Lavreysen, H.; Biesmans, I.; Trabanco, A. A. Bioorg. Med. Chem. Lett. 2010, 20, 175.
doi: 10.1016/j.bmcl.2009.11.008
Hirayama, T.; Okaniwa, M.; Banno, H.; Kakei, H.; Ohashi, A.; Iwai, K.; Ohori, M.; Mori, K.; Gotou, M.; Kawamoto, T.; Yokota, A.; Ishikawa, T. J. Med. Chem. 2015, 58, 8036.
doi: 10.1021/acs.jmedchem.5b00836
Tanaka, M.; Matsugaki, A.; Ishimoto, T.; Nakano, T. J. Bone Miner. Metab. 2016, 34, 234.
doi: 10.1007/s00774-015-0658-2
Okubo, T.; Yoshikawa, R.; Chaki, S.; Okuyama, S.; Nakazato, A. Bioorg. Med. Chem. 2004, 12, 423.
doi: 10.1016/j.bmc.2003.10.050
Mutai, T.; Sawatani, H.; Shida, T.; Shono, H.; Araki, K. J. Org. Chem. 2013, 78, 2482.
doi: 10.1021/jo302711t
Furukawa, S.; Shono, H.; Mutai, T.; Araki, K. ACS Appl. Mater. Interfaces 2014, 6, 16065.
doi: 10.1021/am503956t
Zhou, J.; Liu, J.; Chen, Q. Chin. J. Org. Chem. 2009, 29, 1708(in Chinese).
Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science 2016, 351, 252.
doi: 10.1126/science.aad7893
Wang, X.-C.; Gong, W.; Fang, L.-Z.; Zhu, R.-Y.; Li, S.; Engle, K. M.; Yu, J.-Q. Nature 2015, 519, 334.
doi: 10.1038/nature14214
Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094.
doi: 10.1002/anie.v48:28
Song, G.; Li, X. Acc. Chem. Res. 2015, 48, 1007.
doi: 10.1021/acs.accounts.5b00077
Kuhl, N.; Hopkinson, M. N.; Wencel-Delord, J.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 10236.
doi: 10.1002/anie.201203269
Engle, K. M.; Mei, T.-S.; Wasa, M.; Yu, J.-Q. Acc. Chem. Res. 2011, 45, 788.
Zhang, C.; Tang, C.; Jiao, N. Chem. Soc. Rev. 2012, 41, 3464.
doi: 10.1039/c2cs15323h
Sun, C. L.; Li, B. J.; Shi, Z. J. Chem. Rev. 2011, 111, 1293.
doi: 10.1021/cr100198w
Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879.
doi: 10.1021/cr300153j
Murakami, K.; Yamada, S.; Kaneda, T.; Itami, K. Chem. Rev. 2017, 117, 9302.
doi: 10.1021/acs.chemrev.7b00021
Xi, P.; Yang, F.; Qin, S.; Zhao, D.; Lan, J.; Gao, G.; Hu, C.; You, J. J. Am. Chem. Soc. 2010, 132, 1822.
doi: 10.1021/ja909807f
Wang, P.; Li, G.-C.; Jain, P.; Farmer, M. E.; He, J.; Shen, P.-X.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 14092.
doi: 10.1021/jacs.6b08942
Chu, L.; Qing, F.-L. J. Am. Chem. Soc. 2012, 134, 1298.
doi: 10.1021/ja209992w
Zhu, L.; Cao, X.; Li, Y.; Liu, T.; Wang, X.; Qiu, R.; Yin, S.-F. Chin. J. Org. Chem. 2017, 37, 1613(in Chinese).
Cao, H.; Zhan, H.-Y.; Lin, X.-L.; Du, Z.-D.; Jiang, H.-F. Org. Lett. 2012, 14, 1688.
doi: 10.1021/ol300232a
Fu, H.-Y.; Chen, L.; Doucet, H. J. Org. Chem. 2012, 77, 4473.
doi: 10.1021/jo300528b
Liu, Q. X.; He, B. Y.; Qian, P. C.; Shao, L. X. Org. Biomol. Chem. 2017, 15, 1151.
doi: 10.1039/C6OB02704K
Kalari, S.; Babar, D. A.; Karale, U. B.; Makane, V. B.; Rode, H. B. Tetrahedron Lett. 2017, 58, 2818.
doi: 10.1016/j.tetlet.2017.06.010
Zhao, L.; Zhan, H.; Liao, J.; Huang, J.; Chen, Q.; Qiu, H.; Cao, H. Catal. Commun. 2014, 56, 65.
doi: 10.1016/j.catcom.2014.06.028
Choy, P. Y.; Luk, K. C.; Wu, Y.; So, C. M.; Wang, L.-L.; Kwong, F. Y. J. Org. Chem. 2015, 80, 1457.
doi: 10.1021/jo502386w
Wang, S.; Liu, W.; Cen, J.; Liao, J.; Huang, J.; Zhan, H. Tetrahedron Lett. 2014, 55, 1589.
doi: 10.1016/j.tetlet.2014.01.069
Lei, S.; Cao, H.; Chen, L.-B.; Liu, J.-Y.; Cai, H.-Y.; Tan, J.-W. Adv. Synth. Catal. 2015, 357, 3109.
doi: 10.1002/adsc.201500391
Wang, Z.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2016, 81, 6357.
doi: 10.1021/acs.joc.6b00996
Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
doi: 10.1021/ol049866q
Lixegault, B.; Lapointe, D.; Caron, L.; Vlassova, A.; Fagnou, K. J. Org. Chem. 2009, 74, 1826.
doi: 10.1021/jo8026565
Koszarna, B.; Matczak, R.; Kreszewski, M.; Vakuliuk, O.; Llajn, J.; Tasior, M.; Nowicki, J. T.; Gryko, D. T. Tetrahedron 2014, 70, 225.
doi: 10.1016/j.tet.2013.11.088
Vakuliuk, O.; Koszarna, B.; Gryko, D. T. Adv. Synth. Catal. 2011, 353, 925.
doi: 10.1002/adsc.v353.6
Kazzouli, S. E.; Koubachi, J.; Brahmia, N. E.; Guillaumet, G. RSC Adv. 2015, 5, 15292.
doi: 10.1039/C4RA15384G
Xia, J. B.; You, S. L. Org. Lett. 2009, 11, 1187.
doi: 10.1021/ol9000872
Lapointe, D.; Markiewicz, T.; Whipp, C. J.; Toderian, A.; Fagnou, K. J. Org. Chem. 2011, 76, 749.
doi: 10.1021/jo102081a
Zhang, W.; Liu, F.; Zhao, B. Appl. Organomet. Chem. 2015, 29, 524.
doi: 10.1002/aoc.v29.8
Wang, C.; Jia, H.; Li, Z.; Zhang, H.; Zhao, B. RSC Adv. 2016, 6, 21814.
doi: 10.1039/C5RA25504J
Xia, J. B.; Wang, X. Q.; You, S. L. J. Org. Chem. 2008, 74, 456.
Zhan, H.; Zhao, L.; Li, N.; Chen, L.; Liu, J.; Liao, J.; Cao, H. RSC Adv. 2014, 4, 32013.
doi: 10.1039/C4RA04669B
Cao, H.; Lei, S.; Liao, J.; Huang, J.; Qiu, H.; Chen, Q.; Qiu, S.; Chen, Y. RSC Adv. 2014, 4, 50137.
doi: 10.1039/C4RA09669J
Yang, Y.; Cheng, K.; Zhang, Y. Org. Lett. 2009, 11, 5606.
doi: 10.1021/ol902315w
Hu, H.; Liu, Y.; Zhong, H.; Zhu, Y.; Wang, C.; Ji, M. Chem.-Asian J. 2012, 7, 884.
doi: 10.1002/asia.v7.5
Qi, Z.-S.; Yu, S.-J.; Li, X.-W. J. Org. Chem. 2015, 80, 3471.
doi: 10.1021/acs.joc.5b00059
Li, P.-Y.; Zhang, X.-Y.; Fan, X.-S. J. Org. Chem. 2015, 80, 7508.
doi: 10.1021/acs.joc.5b01092
Ghosh, M.; Naskar, A.; Mishra, S.; Hajra, A. Tetrahedron Lett. 2015, 56, 4101.
doi: 10.1016/j.tetlet.2015.05.028
Li, Y.; Wang, F.; Yu, S.; Li, X. Adv. Synth. Catal. 2016, 358, 880.
doi: 10.1002/adsc.v358.6
Seregin, I. V.; Ryabova, V.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 7742.
doi: 10.1021/ja072718l
Kaswan, P.; Porter, A.; Pericherla, K.; Simone, M.; Peters, S.; Kumar, A.; DeBoef, B. Org. Lett. 2015, 17, 5208.
doi: 10.1021/acs.orglett.5b02539
Kaswan, P.; Nandwana, N. K.; DeBoef, B.; Kumar, A. Adv. Synth. Catal. 2016, 358, 2108.
doi: 10.1002/adsc.v358.13
Wang, S.-C.; Huang, X.-H.; Ge, Z.-M.; Wang, X.; Li, R.-T. RSC Adv. 2016, 6, 63532.
doi: 10.1039/C6RA09046J
Su, H.-M.; Wang, L.-Y.; Rao, H.-H.; Xu, H. Org. Lett. 2017, 19, 2226.
doi: 10.1021/acs.orglett.7b00678
Monir, K.; Bagdi, A. K.; Ghosh, M.; Hajra, A. J. Org. Chem. 2015, 80, 1332.
doi: 10.1021/jo502928e
Wu, Y.; Zhang, H.-R.; Jin, R.-X.; Lan, Q.; Wang, X.-S. Adv. Synth. Catal. 2016, 358, 3528.
doi: 10.1002/adsc.v358.22
Lei, S.; Chen, G.; Mai, Y.; Chen, L.; Cai, H.; Tan, J.; Cao, H. Adv. Synth. Catal. 2016, 358, 67.
doi: 10.1002/adsc.v358.1
Wang, C.; Lei, S.; Cao, H.; Qiu, S.; Liu, J.; Deng, H.; Yan, C. J. Org. Chem. 2015, 80, 12725.
doi: 10.1021/acs.joc.5b02417
Chennapuram, M.; Emmadi, N. R.; Bingi, C.; Atmakur, K. RSC Adv. 2015, 5, 19418.
doi: 10.1039/C4RA15835K
Shakoor, S. A.; Agarwal, D. S.; Kumar, A.; Sakhuja, R. Tetrahedron 2016, 72, 645.
doi: 10.1016/j.tet.2015.12.012
Samanta, S.; Mondal, S.; Santra, S.; Kibriya, G.; Hajra, A. J. Org. Chem. 2016, 81, 10088.
doi: 10.1021/acs.joc.6b02091
Gao, Y.-Y.; Lu, W.-Y.; Liu, P.; Sun, P.-P. J. Org. Chem. 2016, 81, 2482.
doi: 10.1021/acs.joc.6b00046
Lei, S.; Mai, Y.-Y.; Yan, C.-J.; Mao, J.-W.; Cao, H. Org. Lett. 2016, 18, 3582.
doi: 10.1021/acs.orglett.6b01588
Wang, Z.; Li, B.; Zhang, X.; Fan, X. J. Org. Chem. 2016, 81, 6357.
doi: 10.1021/acs.joc.6b00996
Ravi, C.; Mohan, D. C.; Adimurthy, S. Org. Lett. 2014, 16, 2978.
doi: 10.1021/ol501117z
Hiebel, M. A.; Berteina-Raboin, S. Green Chem. 2015, 17, 937.
doi: 10.1039/C4GC01462F
Ji, X. M.; Zhou, S. J.; Chen, F.; Zhang, X. G.; Tang, R. Y. Synthesis 2015, 47, 659.
doi: 10.1055/s-00000084
Bagdi, A. K.; Mitra, S.; Ghosh, M.; Hajra, A. Org. Biomol. Chem. 2015, 13, 3314.
doi: 10.1039/C5OB00033E
Wu, Q.; Zhao, D.; Qin, X.; Lan, J.; You, J. Chem. Commun. 2011, 47, 9188.
doi: 10.1039/c1cc13633j
Ravi, C.; Mohan, D. C.; Adimurthy, S. Org. Biomol. Chem. 2016, 14, 2282.
doi: 10.1039/C5OB02475G
Wu, W.; Ding, Y.; Xie, P.; Tang, Q.; Pittman, J. C.; Zhou, A. Tetrahedron 2017, 73, 2151.
doi: 10.1016/j.tet.2017.02.065
Wang, Q.; Qi, Z.; Xie, F.; Li, X. Adv. Synth. Catal. 2015, 357, 355.
doi: 10.1002/adsc.201400717
Chachignon, H.; Maeno, M.; Kondo, H.; Shibata, N.; Cahard, D. Org. Lett. 2016, 18, 2467.
doi: 10.1021/acs.orglett.6b01026
Mitra, S.; Ghosh, M.; Mishra, S.; Hajra, A. J. Org. Chem. 2015, 80, 8275.
doi: 10.1021/acs.joc.5b01369
Yang, D.; Yan, K.; Wei, W.; Li, G.; Lu, S.; Zhao, C.; Tian, L.; Wang, H. J. Org. Chem. 2015, 80, 11073.
doi: 10.1021/acs.joc.5b01637
Zhang, H.; Wei, Q.; Wei, S.; Qu, J.; Wang, B. Eur. J. Org. Chem. 2016, 3373.
Rafique, J.; Saba, S.; Rosário, A. R.; Braga, A. L. Chem.-Eur J. 2016, 22, 11854.
doi: 10.1002/chem.201600800
Sun, P.-F.; Jiang, M.; Wei, W.; Min, Y.-Y.; Zhang, W.; Li, W.-H.; Yang, D.-S.; Wang, H. J. Org. Chem. 2017, 82, 2906.
doi: 10.1021/acs.joc.6b02865
Yang, D.-S.; Yan, K.-L.; Wei, W.; Liu, Y.; Zhang, M.-Q.; Zhao, C.-X.; Tian, L.-J.; Wang, H. Synthesis 2016, 48, 122.
Hao, X.-Q.; Liu, W.-B.; Shen, X.-J.; Wang, W.; Liang, Z.-K.; Zhu, X.-J.; Song, M.-P. J. Saudi Chem. Soc. 2017, 21, 91.
doi: 10.1016/j.jscs.2016.02.004
Mondal, S.; Samanta, S.; Jana, S.; Hajra, A. J. Org. Chem. 2017, 82, 4504.
doi: 10.1021/acs.joc.7b00564
Gao, Y.; Chen, S.; Lu, W.; Gu, W.; Liu, P.; Sun, P. Org. Biomol. Chem. 2017, 15, 8102.
doi: 10.1039/C7OB02029E
Yadav, M.; Dara, S.; Saikam, V.; Kumar, M.; Aithagani, S. K.; Paul, S.; Vishwakarma, R. A.; Singh, P. P. Eur. J. Org. Chem. 2015, 6526.
Danqing Wu , Jiajun Liu , Tianyu Li , Dazhen Xu , Zhiwei Miao . Research Progress on the Simultaneous Construction of C—O and C—X Bonds via 1,2-Difunctionalization of Olefins through Radical Pathways. University Chemistry, 2024, 39(11): 146-157. doi: 10.12461/PKU.DXHX202403087
Liyang ZHANG , Dongdong YANG , Ning LI , Yuanyu YANG , Qi MA . Crystal structures, luminescent properties and Hirshfeld surface analyses of three cadmium(Ⅱ) complexes based on 2-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)benzoate. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1943-1952. doi: 10.11862/CJIC.20240079
Yuanyuan Ping , Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092
Hui Wang , Abdelkader Labidi , Menghan Ren , Feroz Shaik , Chuanyi Wang . 微观结构调控的g-C3N4在光催化NO转化中的最新进展:吸附/活化位点的关键作用. Acta Physico-Chimica Sinica, 2025, 41(5): 100039-. doi: 10.1016/j.actphy.2024.100039
Tong Li , Leping Pan , Yan Zhang , Jihu Su , Kai Li , Kuiliang Li , Hu Chen , Qi Sun , Zhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897
Tao Zhou , Jing Zhou , Yunyun Liu , Jie-Ping Wan , Fen-Er Chen . Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C–H functionalization and chromone annulation of enaminones. Chinese Chemical Letters, 2024, 35(11): 109683-. doi: 10.1016/j.cclet.2024.109683
Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543
Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
Lei Wan , Yizhou Tong , Xi Lu , Yao Fu . Cobalt-catalyzed reductive alkynylation to construct C(sp)-C(sp3) and C(sp)-C(sp2) bonds. Chinese Chemical Letters, 2024, 35(7): 109283-. doi: 10.1016/j.cclet.2023.109283
Ke-Ai Zhou , Lian Huang , Xing-Ping Fu , Li-Ling Zhang , Yu-Ling Wang , Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172
Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
Huakang Zong , Xinyue Li , Yanlin Zhang , Faxun Wang , Xingxing Yu , Guotao Duan , Yuanyuan Luo . Pt/Ti3C2 electrode material used for H2S sensor with low detection limit and high stability. Chinese Chemical Letters, 2025, 36(5): 110195-. doi: 10.1016/j.cclet.2024.110195
Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
Yujia Shi , Yan Qiao , Pengfei Xie , Miaomiao Tian , Xingwei Li , Junbiao Chang , Bingxian Liu . Rhodium-catalyzed enantioselective in situ C(sp3)−H heteroarylation by a desymmetrization approach. Chinese Chemical Letters, 2024, 35(10): 109544-. doi: 10.1016/j.cclet.2024.109544
Jinpeng Du , Junlin Chen , Yulong Shan , Tongliang Zhang , Yu Sun , Zhongqi Liu , Xiaoyan Shi , Wenpo Shan , Yunbo Yu , Hong He . Insight into the effects of C3H6 on fresh and hydrothermally aged Cu-SSZ-39 catalysts. Chinese Chemical Letters, 2025, 36(3): 110019-. doi: 10.1016/j.cclet.2024.110019
Guangming YIN , Huaiyao WANG , Jianhua ZHENG , Xinyue DONG , Jian LI , Yi'nan SUN , Yiming GAO , Bingbing WANG . Preparation and photocatalytic degradation performance of Ag/protonated g-C3N4 nanorod materials. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1491-1500. doi: 10.11862/CJIC.20240086
Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H2O and Its Intermediates on Electron-Deficient Mn(3+δ)+ for Efficient Photocatalytic H2O2 Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
Hualin Jiang , Wenxi Ye , Huitao Zhen , Xubiao Luo , Vyacheslav Fominski , Long Ye , Pinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984
Yuemin Chen , Yunqi Wu , Guoao Wang , Feihu Cui , Haitao Tang , Yingming Pan . Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3)-H bonds enabled by organocatalysis. Chinese Chemical Letters, 2024, 35(9): 109445-. doi: 10.1016/j.cclet.2023.109445