Recent Advances in N-Phenoxyacetamides Directed C-H Bond Functionalizations
- Corresponding author: Hu Fangdong, hufangdong@lyu.edu.cn
Citation:
Jiang Xiaolei, Hao Jiaqi, Zhou Guoqing, Hou Chengcheng, Hu Fangdong. Recent Advances in N-Phenoxyacetamides Directed C-H Bond Functionalizations[J]. Chinese Journal of Organic Chemistry,
;2019, 39(7): 1811-1830.
doi:
10.6023/cjoc201902019
For selected reviews: (a) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. 2010, 110, 624.
(b) Colby, D. A.; Tsai, A. S.; Bergman, R. G.; Ellman, J. A. Acc. Chem. Res. 2012, 45, 814.
(c) Song, G.; Wang, F.; Li, X. Chem. Soc. Rev. 2012, 41, 3651.
(d) Gensch, T.; Hopkinson, M. N.; Glorius, F.; Wencel-Delord, J. Chem. Soc. Rev. 2016, 45, 2900.
(e) Gulías, M.; Mascareñas, J. L. Angew. Chem. Int. Ed. 2016, 55, 11000.
(f) Hummel, J. R.; Boerth, J. A.; Ellman, J. A. Chem. Rev. 2017, 117, 9163.
For reviews, see: (a) Huang, H.; Ji, X.; Wu, W.; Jiang, H. Chem. Soc. Rev. 2015, 44, 1155.
(b) Hu, Z.; Tong, X.; Liu, G. Chin. J. Org. Chem. 2015, 35, 539(in Chinese).
(胡志勇, 童晓峰, 刘桂霞, 有机化学, 2015, 35, 539.)
(c) Mo, J.; Wang, L.; Liu, Y.; Cui, X. Synthesis 2015, 47, 439.
(d) Sun, H.; Huang, Y. Synlett 2015, 26, 2751.
Liu, G.; Shen, Y.; Zhou, Z.; Lu, X. Angew. Chem. Int. Ed. 2013, 52, 6033.
doi: 10.1002/anie.201300881
Yang, Y.-F.; Houk, K. N.; Wu, Y.-D. J. Am. Chem. Soc. 2016, 138, 6861.
doi: 10.1021/jacs.6b03424
Chen, Y.; Wang, D.; Duan, P.; Ben, R.; Dai, L.; Shao, X.; Hong, M.; Zhao, J.; Huang, Y. Nat. Commun. 2014, 5, 4610.
doi: 10.1038/ncomms5610
Zhou, Z.; Liu, G.; Shen, Y.; Lu, X. Org. Chem. Front. 2014, 1, 1161.
doi: 10.1039/C4QO00196F
Zhou, Z.; Liu, G.; Chen, Y.; Lu, X. Org. Lett. 2015, 17, 5874.
doi: 10.1021/acs.orglett.5b03060
Xie, Y. Chem. Commun. 2016, 52, 12372.
doi: 10.1039/C6CC05769A
Yi, W.; Chen, W.; Liu, F.-X.; Zhong, Y.; Wu, D.; Zhou, Z.; Gao, H. ACS Catal. 2018, 8, 9508.
doi: 10.1021/acscatal.8b02402
Chen, W.; Liu, F.-X.; Gong, W.; Zhou, Z.; Gao, H.; Shi, J.; Wu, B.; Yi, W. Adv. Synth. Catal. 2018, 360, 2470.
doi: 10.1002/adsc.201800322
Zhou, W.; Mei, Y.-L.; Li, B.; Guan, Z.-Y.; Deng, Q.-H. Org. Lett. 2018, 20, 5808.
doi: 10.1021/acs.orglett.8b02504
Wang, H.; Wang, B.; Li, B. J. Org. Chem. 2017, 82, 9560.
doi: 10.1021/acs.joc.7b01566
Li, Y.; Shi, D.; Tang, Y.; He, X.; Xu, S. J. Org. Chem. 2018, 83, 9464.
doi: 10.1021/acs.joc.8b01166
Li, Y.; Shi, D.; He, X.; Wang, Y.; Tang, Y.; Zhang, J.; Xu, S. J. Org. Chem. 2019, 84, 1588.
doi: 10.1021/acs.joc.8b02661
Zhou, J.; Shi, J.; Qi, Z.; Li, X.; Xu, H. E.; Yi, W. ACS Catal. 2015, 5, 6999.
doi: 10.1021/acscatal.5b01571
Shen, Y.; Liu, G.; Zhou, Z.; Lu, X. Org. Lett. 2013, 15, 3366.
doi: 10.1021/ol4014188
Hu, Z.; Tong, X.; Liu, G. Org. Lett. 2016, 18, 1702.
doi: 10.1021/acs.orglett.6b00616
Li, Y.; Tang, Y.; He, X.; Shi, D.; Wu, J.; Xu, S. Chem. Eur. J. 2017, 23, 7453.
doi: 10.1002/chem.201701703
Prakash, S.; Muralirajan, K.; Cheng, C.-H. Chem. Commun. 2015, 51, 13362.
doi: 10.1039/C5CC04211A
Wang, Y.; Chen, Y.; Yang, Y.; Zhou, B. Org. Chem. Front. 2018, 5, 1844.
doi: 10.1039/C8QO00265G
Zhou, Z.; Bian, M.; Zhao, L.; Gao, H.; Huang, J.; Liu, X.; Yu, X.; Li. X.; Yi, W. Org. Lett. 2018, 20, 3892.
doi: 10.1021/acs.orglett.8b01477
Zhang, H.; Wang, K.; Wang, B.; Yi, H.; Hu, F.; Li, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 13234.
doi: 10.1002/anie.201408555
Guo, W.; Xia, Y. J. Org. Chem. 2015, 80, 8113.
doi: 10.1021/acs.joc.5b01201
Li, J.; Qiu, Z. J. Org. Chem. 2015, 80, 10686.
doi: 10.1021/acs.joc.5b01895
Wang, X.; Lerchen, A.; Daniliuc, C. G.; Glorius, F. Angew. Chem., Int. Ed. 2018, 57, 1712.
doi: 10.1002/anie.201712019
Wang, X.; Lerchen, A.; Gensch, T.; Knecht, T.; Daniliuc, C. G.; Glorius, F. Angew. Chem. Int. Ed. 2017, 56, 1381.
doi: 10.1002/anie.201610117
Wang, X.; Li, Y.; Knecht, T.; Daniliuc, C. G.; Houk, K. N.; Glorius, F. Angew. Chem. Int. Ed. 2018, 57, 5520.
doi: 10.1002/anie.201800803
Duan, P.; Lan, X.; Chen, Y.; Qian, S.-S.; Li, J. J.; Lu, L.; Lu, Y.; Chen, B.; Hong, M.; Zhao, J. Chem. Commun. 2014, 50, 12135.
doi: 10.1039/C4CC05485G
Lerchen, A.; Knecht, T.; Daniliuc, C. G.; Glorius, F. Angew. Chem., Int. Ed. 2016, 55, 15166.
doi: 10.1002/anie.201608729
Hu, F.; Xia, Y.; Ye, F.; Liu, Z.; Ma, C.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2014, 53, 1364.
doi: 10.1002/anie.201309650
Zhang, Y.; He, Y.; Li, L.; Ji, M.; Li, X.-Z.; Zhu, G. J. Org. Chem. 2018, 83, 2898.
doi: 10.1021/acs.joc.8b00108
Zhou, J.; Shi, J.; Liu, X.; Jia, J.; Song, H.; Xu, H. E.; Yi, W. Chem. Commun. 2015, 51, 5868.
doi: 10.1039/C5CC00354G
Hu, Z.; Liu, G. Adv. Synth. Catal. 2017, 359, 1643.
doi: 10.1002/adsc.201601296
Wu, Y.; Chen, Z.; Yang, Y.; Zhu, W.; Zhou, B. J. Am. Chem. Soc. 2018, 140, 42.
doi: 10.1021/jacs.7b10349
Duan, P.; Yang, Y.; Ben, R.; Yan, Y.; Dai, L.; Hong, M.; Wu, Y.-D.; Wang, D.; Zhang, X.; Zhao, J. Chem. Sci. 2014, 5, 1574.
doi: 10.1039/C3SC53228C
Li, B.; Lan, J.; Wu, D.; You, J. Angew. Chem., Int. Ed. 2015, 54, 14008.
doi: 10.1002/anie.201507272
Li, B.; Tang, G.; Zhou, L.; Wu, D.; Lan, J.; Zhou, L.; Lu, Z.; You, J. Adv. Funct. Mater. 2017, 27, 1605245.
doi: 10.1002/adfm.201605245
Wu, Q.; Chen, Y.; Yan, D.; Zhang, M.; Lu, Y.; Sun, W.-Y.; Zhao, J. Chem. Sci. 2017, 8, 169.
doi: 10.1039/C6SC03169B
Wang, X.; Gensch, T.; Lerchen, A.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2017, 139, 6506.
doi: 10.1021/jacs.7b02725
Wu, Q.; Yan, D.; Chen, Y.; Wang, T.; Xiong, F.; Wei, W.; Lu, Y.; Sun, W.-Y.; Li, J. J.; Zhao, J. Nat. Commun. 2017, 8, 14227.
doi: 10.1038/ncomms14227
Hu, S.; Lu, L.; Zhu, T.; Wu, Q.; Chen, Y.; Li, J. J.; Zhao, J. Org. Biomol. Chem. 2018, 16, 43.
doi: 10.1039/C7OB02438J
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
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
Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
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
Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
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
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
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
Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
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
Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
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
.
CCS Chemistry | 超分子活化底物为自由基促进高效选择性光催化氧化
. CCS Chemistry, 2025, 7(10.31635/ccschem.025.202405229): -.Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C3N4纳米片及其高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
Shuai Tang , Zian Wang , Mengyi Zhu , Xinyun Zhao , Xiaoyun Hu , Hua Zhang . Synthesis of organoboron compounds via heterogeneous C–H and C–X borylation. Chinese Chemical Letters, 2025, 36(5): 110503-. doi: 10.1016/j.cclet.2024.110503
. . Chinese Journal of Inorganic Chemistry, 2024, 40(11): 0-0.
Zhanggui DUAN , Yi PEI , Shanshan ZHENG , Zhaoyang WANG , Yongguang WANG , Junjie WANG , Yang HU , Chunxin LÜ , Wei ZHONG . Preparation of UiO-66-NH2 supported copper catalyst and its catalytic activity on alcohol oxidation. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 496-506. doi: 10.11862/CJIC.20230317
Qingqing SHEN , Xiangbowen DU , Kaicheng QIAN , Zhikang JIN , Zheng FANG , Tong WEI , Renhong LI . Self-supporting Cu/α-FeOOH/foam nickel composite catalyst for efficient hydrogen production by coupling methanol oxidation and water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1953-1964. doi: 10.11862/CJIC.20240028
Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-based Photocatalysts for CO2 Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-. doi: 10.3866/PKU.WHXB202406029
Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063