Progress in Co-Catalyzed C-H Amination
- Corresponding author: He Yide, heyd@njtech.edu.cn Huang Fei, huangfei0208@yeah.net
Citation:
Sun Yiming, Ding Qifeng, Yu Yang, He Yide, Huang Fei. Progress in Co-Catalyzed C-H Amination[J]. Chinese Journal of Organic Chemistry,
;2019, 39(12): 3363-3374.
doi:
10.6023/cjoc201906026
(a) Ning, Z.; Tian, H. Chem. Commun. 2009, 5483.
(b) Michael, J. P. Nat. Prod. Rep. 2008, 25, 166.
(c) Liu, D.; Zhang, Z.; Zhang, H.; Wang, Y. Chem. Commun. 2013, 49, 10001.
(d) Mphahlele, M. J.; Paumo, H. K.; El-Nahas, A. M.; ElHendawy, M. M. Molecules 2014, 19, 795.
(e) Lücking, U. Angew. Chem., Int. Ed. 2013, 52, 9399.
(f) Liu, L.-T.; Chen, Y.-Y.; Zhang, A.-A.; Liu, X.; Zhang, L.; Bai, J.-R.; Li, H.; Mao, G.-L. Chin. J. Org. Chem. 2019, 39, 475(in Chinese).
(刘澜涛, 陈莹莹, 张安安, 刘雪, 张丽, 白静茹, 李恒, 毛国梁, 有机化学, 2019, 39, 475.)
(a) Dillard, R.; Yen, T.; Stark, P.; Pavey, D. J. Med. Chem. 1980, 23, 717.
(b) Zhou, H.; Chen, Z.-Y. Chin. J. Org. Chem. 2018, 38, 719(in Chinese).
(周豪, 陈知远, 有机化学, 2018, 38, 719.)
Bartoszyk, G.; Dooley, D.; Barth, H.; Hartenstein, J.; Satzinger, G. J. Pharm. Pharmacol. 1987, 39, 407.
doi: 10.1111/j.2042-7158.1987.tb03410.x
(a) Achelle, S.; Rodríguez-Lopez, J.; Guen, F. R. J. Org. Chem. 2014, 79, 7564.
(b) Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7, 659.
(a) Strohriegl, P.; Grazulevicius, J. V. Adv. Mater. 2002, 14, 1439.
(b) Nishimura, K.; Kobota, T.; Inada, H.; Shirota, Y. J. Mater. Chem. 1991, 1, 897
(a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
(b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
(c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
(d) Hartwig, J. F. Nature 2008, 455, 314.
(a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247.
(b) Moselage, M.; Li, J.; Ackermann, L. ACS Catal. 2016, 6, 498.
(c) Zhao, F.-Q.; Yang, Q.; Zhang, J.-J.; Shi, W.-M.; Hu, H.-H.; Liang, F.; Wei, W.; Zhou, S.-L. Org. Lett. 2018, 20, 7753.
(d) Gao, F.; Han, X.; Li, C.-P.; Liu, L.-J.; Cong, Z.-Q.; Liu, H. RSC Adv. 2018, 8, 32659.
(e) Yetra, S. R.; Shen, Z.-G.; Wang, H.; Ackermann, L. Beilstein J. Org. Chem. 2018, 14, 1546.
(f) Wang, F.; Jin, L.; Kong, L.-H.; Li, X.-W. Org. Lett. 2017, 19, 1812.
(g) Mei, R.-H.; Loup, J.; Ackermann, L. ACS Catal. 2016, 6, 793.
(h) Zhang, L.-B.; Zhang, S.-K.; Wei, D.-H.; Zhu, X.-J.; Hao, X.-Q.; Su, J.-H.; Niu, J.-L.; Song, M.-P. Org. Lett. 2016, 18, 1318.
(i) Sun, J.-S.; Liu, M.; Zhang, J.; Dong, L. J. Org. Chem. 2018, 83, 10555.
(a) Kuhl, N.; Schröder, N.; Glorius, F. Adv. Synth. Catal. 2014. 356 1443.
(b) Song, G.; Li, X. Acc. Chem. Res. 2015. 48 1007.
(c) Newton, C. G.; Wang, S.-G.; Oliveira, C. C.; Cramer, N. Chem. Rev. 2017. 117, 8908.
(d) Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Chem. Rev. 2017. 117, 9163.
(a) Gandeepan, P.; Cheng, C. H. Acc. Chem. Res. 2015, 48, 1194.
(b) Grigorjeva, L.; Daugulis, O. Org. Lett. 2014, 16, 4684.
(c) Prakash, S.; Muralirajan, K.; Cheng, C. H. Angew. Chem., Int. Ed. 2016, 55, 1844.
(d) Zhang, Z.-Z.; Liu, B.; Xu, J.-W.; Yan, S.-Y.; Shi, B.-F. Org. Lett. 2016, 18, 1776.
(e) Wei, D.-H.; Zhu, X.-J.; Niu, J.-L.; Song, M.-P. ChemCatChem 2016, 8, 1242.
(f) Shin, K.; Kim, H.; Chang, S. Acc. Chem. Res. 2015, 48, 1040.
(g) Kim, H.; Chang, S. ACS Catal. 2016, 6, 2341.
(h) Gu, Z.-Y.; Ji, S.-J. Acta Chim. Sinica 2018, 76, 347(in Chinese).
(顾正洋, 纪顺俊, 化学学报, 2018, 76, 347.)
(i) Zhang, J.-H.; Hao, X.-Q.; Wang, Z.-L.; Ren, C.-J.; Niu, J.-L.; Song, M.-P. Chin. J. Org. Chem. 2017, 37, 1237(in Chinese).
(张家恒, 郝新奇, 王正龙, 任常久, 牛俊龙, 宋毛平, 有机化学, 2017, 37, 1237.)
(j) Cheng, B.; Lu, P.; Zhao, J.-J.; Lu, Z. Chin. J. Org. Chem. 2019, 39, 1704(in Chinese).
(程彪, 陆鹏, 赵家金, 陆展, 有机化学, 2019, 39, 1704.)
(a) Park, J.; Chang, S. Angew. Chem., Int. Ed. 2015, 54, 14103.
(b) Liang, Y.-J.; Liang, Y.-F.; Tang, C.-H.; Yuan, Y.-Z.; Jiao, N. Chem. Eur. J. 2015, 21, 16395.
(d) Wu, F.-F.; Zhao, Y.; Chen, W.-Z. Tetrahedron 2016, 72, 8004.
(e) Wang, F.; Wang, H.; Wang, Q.; Yu, S.-J.; Li, X.-W. Org. Lett. 2016, 18, 1306.
(g) Figg, T. M.; Park, S.; Park, J.; Chang, S.; Musaev, D. G. Organometallics 2014, 33, 4076.
(h) Liu, Y.; Xie, F.; Jia, A.-Q.; Li, X.-W. Chem. Commun. 2018, 54, 4345.
(i) Bera, S. S.; Sk, M. R.; Maji, M. S. Chem. Eur. J. 2019, 25, 1806.
(j) Yan, Q.-Q.; Xiao, T.-X.; Liu, Z.-X.; Zhang, Y.-H. Adv. Synth. Catal. 2016, 358, 2707.
(k) Cheng, H.-C.; Hernández, J. G.; Bolm, C. Adv. Synth. Catal. 2018, 360, 1.
(l) Borah, G.; Borah, P.; Patel, P. Org. Biomol. Chem. 2017, 15, 3854.
(m) Yu, X.-L.; Ma, Q.; Lv, S.-Y.; Li, J.; Zhang, C.; Hai, L.; Wang, Q.-T.; Wu, Y. Org. Chem. Front. 2017, 4, 2184.
(n) Shi, P.-F.; Wang, L.-L.; Chen, K.-H.; Wang, J.; Zhu, J. Org. Lett. 2017, 19, 2418.
(a) Villanueva, O.; Weldy, N. M.; Blakey, S. B.; MacBeth, C. E. Chem. Sci. 2015, 6, 6672.
(b) Harden, J. D.; Ruppel, J. V.; Gao, G.-Y.; Zhang, X. P. Chem. Commun. 2007, 4644.
(c) Pang, S.-F.; Yuan, H.-K.; Wu, Y.-J.; Shi, F. J. Mol. Catal. 2017, 31, 105(in Chinese).
(庞少峰, 袁航空, 吴亚娟, 石峰, 分子催化, 2017, 31, 105.)
(d) Wu, X.-S.; Yang, K.; Zhao, Y.; Sun, H.; Li, G.-G.; Ge, H.-B. Nat. Commun. 2015, 6, 6462.
(e) Lu, H.-J.; Li, C.-Q.; Jiang, H.-L.; Lizardi, C. L.; Zhang, X. P. Angew. Chem., Int. Ed. 2014, 53, 7028.
(f) Lu, H.-J.; Zhang, X. P. Chem. Soc. Rev. 2011, 40, 1899.
(g) Ragaini, F.; Penoni, A.; Gallo, E.; Tollari, S.; Gotti, C. L.; Lapadula, M.; Mangioni, E.; Cenini, S. Chem. Eur. J. 2003, 9, 249.
(h) Cenini, S.; Tollari, S.; Penoni, A.; Cereda C. J. Mol. Catal. 1999, 137, 135.
(i) Ruppel, J. V.; Kamble, R. M.; Zhang, X. P. Org. Lett. 2007, 9, 4889.
(j) Lu, H.-J.; Tao, J.; Jones, J. E.; Wojtas, L.; Zhang, X. P. Org. Lett. 2010, 12, 1248.
(k) Lu, H.-J.; Subbarayan, V.; Tao, J.; Zhang, X. P. Organometallics 2010, 29, 389.
(l) Cenini, S.; Gallo, E.; Penoni, A.; Ragainia, F.; Tollari, S. Chem. Commun. 2000, 2265.
(m) Tan, P.-W.; Mak, A. M.; Sullivan, M. B.; Dixon, D. J.; Seayad, J. Angew. Chem., Int. Ed. 2017, 56, 16550.
(n) Lu, H.-J.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2010, 49, 10192.
Patel, P.; Chang, S. ACS Catal. 2015, 5, 853.
doi: 10.1021/cs501860b
Wang, X.-M.; Lerchen, A.; Glorius, F. Org. Lett. 2016, 18, 2090.
doi: 10.1021/acs.orglett.6b00716
Wang, H.; Lorion, M.-M.; Ackermann, L. Angew. Chem., Int. Ed. 2016, 55, 10386.
doi: 10.1002/anie.201603260
Huang, J.-p.; Huang, Y.-F.; Wang, T.; Huang, Q.; Wang, Z.-H.; Chen, Z.-Y. Org. Lett. 2017, 19, 1128.
doi: 10.1021/acs.orglett.7b00120
Du, C.; Li, P.-X.; Zhu, X.-J.; Han, J.-N.; Niu, J.-L.; Song, M.-P. ACS Catal. 2017, 7, 2810.
doi: 10.1021/acscatal.7b00262
Sauermann, N.; Mei, R.-H.; Ackermann, L. Angew. Chem., Int. Ed. 2018, 57, 5090.
doi: 10.1002/anie.201802206
(a) Parry, J. B.; Fu, N.; Lin, S. Synlett 2018, 29, 257.
(b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117, 13230.
(c) Feng, R.; Smith, J. A.; Moeller, K. D. Acc. Chem. Res. 2017, 50, 2346.
(d) Jiao, K.-J.; Zhao, C.-Q.; Fang, P.; Mei, T.-S. Tetrahedron Lett. 2017, 58, 797.
(e) Hou, Z.-W.; Mao, Z.-Y.; Xu, H.-C. Synlett 2017, 28, 1867.
Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Adv. Synth. Catal. 2014, 356, 1491.
doi: 10.1002/adsc.201301110
Li, W.; Weng, L.; Jin, G. Inorg. Chem. Commun. 2004, 7, 1174.
doi: 10.1016/j.inoche.2004.09.005
Sun, B.; Yoshino, T.; Matsunaga, S.; Kanai, M. Chem. Commun. 2015, 51, 4659.
doi: 10.1039/C4CC10284C
Gao, X.-L.; Wang, P.; Zeng, L.; Tang, S.; Lei, A.-W. J. Am. Chem. Soc. 2018, 140, 4195.
doi: 10.1021/jacs.7b13049
Wang, S.-B.; Gu, Q.; You, S.-L. J. Catal. 2018, 361, 393.
doi: 10.1016/j.jcat.2018.03.007
Huang, D.-Y.; Yao, Q.-J.; Zhang, S.; Xu, X.-T.; Zhang, K.; Shi, B.-F. Org. Lett. 2019, 21, 951.
doi: 10.1021/acs.orglett.8b03938
Lu, H.-J.; Hu, Y.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Org. Lett. 2012, 14, 5158.
doi: 10.1021/ol302511f
Luo, Y.-R. In Comprehensive Handbook of Chemical Bond Energies, Vol. 3, Ed.: Luo, Y.-R., Taylor & Francis Group, Boca Raton, 2007, p. 19.
Barsu, N.; Rahman, M. A.; Sen, M.; Sundararaju B. Chem. Eur. J. 2016, 22, 9135.
doi: 10.1002/chem.201601597
Lu, H.-J.; Lang, K.; Jiang, H.-L.; Wojtas, L.; Zhang, X. P. Chem. Sci. 2016, 7, 6934.
doi: 10.1039/C6SC02231F
Li, C.-Q.; Lang, K.; Lu, H.-J.; Hu, Y.; Cui, X.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2018, 57, 16837.
doi: 10.1002/anie.201808923
Fukagawa, S.; Kato, Y.; Tanaka, R.; Kojima, M.; Yoshino, T.; Matsunaga. S. Angew. Chem., Int. Ed. 2019, 58, 1153.
doi: 10.1002/anie.201812215
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
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
Hao Wu , Zhen Liu , Dachang Bai . 1H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
Nan Xiao , Fang Sun . 二芳基硫醚化合物的构建及应用. University Chemistry, 2025, 40(6): 360-363. doi: 10.12461/PKU.DXHX202407099
Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO3/SiO2. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
Xiaofang Li , Zhigang Wang . Modulating dz2-orbital occupancy of Au cocatalysts for enhanced photocatalytic H2O2 production. Acta Physico-Chimica Sinica, 2025, 41(7): 100080-. doi: 10.1016/j.actphy.2025.100080
Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn2S4 photocatalyst for H2O2 production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
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