Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C—C Bonds Activation Reactions
- Corresponding author: Wang Jianhui, wangjingjing0918@163.com
Citation:
Wang Jingjing, Li Feng, Yu Xiaobo, Liu Lantao, Ding Junru, Xie Peiyao, Wang Jianhui. Recent Progress in the Research of the Transition-Metal-Catalyzed N-Directed Carbonyl and Alcohol Hydroxyl ortho C—C Bonds Activation Reactions[J]. Chinese Journal of Organic Chemistry,
;2018, 38(7): 1638-1649.
doi:
10.6023/cjoc201802007
Bard, A. J.; Whitesides, G. M.; Zare, R. N.; McLaffertv, F. W. Acc. Chem. Res. 1995, 28, 91.
doi: 10.1021/ar00051a001
Xu, Z.-J.; Jiao, N. Sci. Sin. Chim. 2013, 43, 1121 (in Chinese).
Suggs, J. W.; Jun, C.-H. J. Am. Chem. Soc. 1984, 106, 3054.
doi: 10.1021/ja00322a063
Suggs, J. W.; Jun, C.-H. J. Chem. Soc., Chem. Commun. 1985, 92.
Wentzel, M. T.; Reddy, V. J.; Hyster, T. K.; Douglas, C. J. Angew. Chem., Int. Ed. 2009, 48, 6121.
doi: 10.1002/anie.v48:33
Dreis, A. M.; Douglas, C. J. J. Am. Chem. Soc. 2009, 131, 412.
doi: 10.1021/ja8066308
Rathbun, C. M.; Johnson, J. B. J. Am. Chem. Soc. 2011, 133, 2031.
doi: 10.1021/ja109686v
Dennis, J. M.; Compager, C. T.; Dorn, S. K.; Johnson, J. B. Org. Lett. 2016, 18, 3334.
doi: 10.1021/acs.orglett.6b01434
Li, H.; Zhang, X.-S.; Chen, K.; Wang, X. Shi, Z.-J. J. Am. Chem. Soc. 2011, 133, 15244.
doi: 10.1021/ja205228y
Chen, K.; Li, H.; Li, Y.; Zhang, X.-S.; Lei, Z.-Q.; Shi, Z.-J. Chem. Sci. 2012, 3, 1645.
doi: 10.1039/c2sc00923d
Zhang, X.-S.; Li, Y.; Li, H.; Chen, K.; Lei, Z.-Q.; Shi, Z.-J. Chem. Eur. J. 2012, 18, 16214.
doi: 10.1002/chem.v18.50
Chen, K.; Li, H.; Lei, Z.-Q.; Li, Y.; Ye, W.-H.; Zhang, L.-S.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 9851.
doi: 10.1002/anie.201204338
Lei, Z.-Q.; Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Sun, J.; Shi, Z.-J. Angew. Chem., Int. Ed. 2012, 51, 2690.
doi: 10.1002/anie.201107136
Lei, Z.-Q; Pan, F.; Li, H.; Li, Y.; Zhang, X.-S.; Chen, K.; Wang, X.; Li, Y.-X.; Sun, J.; Shi, Z.-J. J. Am. Chem. Soc. 2015, 137, 5012.
doi: 10.1021/ja512003d
Wang, J.; Chen, W.; Zuo, S.; Liu, L.; Zhang, X.; Wang, J. Angew. Chem., Int. Ed. 2012, 51, 12334.
doi: 10.1002/anie.v51.49
(a) Zarghi, A. ; Ghodsi, R. Bioorg. Med. Chem. 2010, 18, 5855.
(b) Nien, C. -Y. ; Chen, Y. -C. ; Kuo, C. -C. ; Hsieh, H. -P. ; Chang, C. -Y. ; Wu, J. -S. ; Wu, S. -Y. ; Liou, J. -P. ; Chang, J. -Y. J. Med. Chem. 2010, 53, 2309.
Thomas, B. C. ; James, C. A. ; Karol, D. E. ; Ulrich, S. WO 2002042248, 2002 [Chem. Abstr. 2002, 137, 6003].
Teruo, O. ; Shigeki, S. ; Takayuki, I. ; Yasuji, U. ; Tatsuya, Y. ; Noriko, Y. JP 10291988A, 1998 [Chem. Abstr. 1998, 130, 24979].
Yasuo, O. ; Juji, N. ; Haruki, T. ; Naokatsu, S. ; Hiroshi, K. ; Shunei, Y. ; Akio, I. JP 07173138A, 1995[Chem. Abstr. 1995, 123, 313777].
(a) Dowerah, D. ; Radonovich, L. J. ; Woolsey, N. F. Organometallics 1990, 9, 614.
(b) Omae, I. Chem. Rev. 1979, 79, 287.
(a) Ueura, K. ; Satoh, T. ; Miura, M. J. Org. Chem. 2007, 72, 5362.
(b) Ueura, K. ; Satoh, T. ; Miura, M. Org. Lett. 2007, 9, 1407.
(c) Kisenyi, J. M. ; Sunley, G. J. ; Cabeza, J. A. ; Smith, A. J. ; Adams, H. ; Salt, N. J. ; Maitlis, P. M. J. Chem. Soc., Dalton Trans. 1987, 2459.
Wang, J.; Liu, B.; Zhao, H.; Wang, J. Organometallics 2012, 31, 8598.
doi: 10.1021/om300994j
Lipshutz, B. H.; Frieman, B.; Birkedal, H. Org. Lett. 2004, 6, 2305.
doi: 10.1021/ol049681j
Yu, X. B.; Wang, J. J.; Guo, W. J.; Tian, Y.; Wang, J. Organometallics 2016, 35, 1876.
doi: 10.1021/acs.organomet.6b00238
Zhao, T.-T.; Xu, W.-H.; Zheng, Z.-J.; Xu, P.-F.; Wei, H. J. Am. Chem. Soc. 2018, 140, 586.
doi: 10.1021/jacs.7b11591
Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1999, 121, 8645.
doi: 10.1021/ja992048m
Gribkov, D. V.; Pastine, S. J.; Schnürch, M.; Sames, D. J. Am. Chem. Soc. 2007, 129, 11750.
doi: 10.1021/ja072577n
Niwa, T.; Yorimitsu, H.; Oshima, K. Angew. Chem., Int. Ed. 2007, 46, 2643.
doi: 10.1002/(ISSN)1521-3773
(a) Jun, C. -H. ; Lee, H. ; Hong, J. -B. J. Org. Chem. 1997, 62, 1200.
(b) Ahn, J. -A. ; Chang, D. -H. ; Park, Y. J. ; Yon, Y. R. ; Loupy, A. ; Jun, C. -H. Adv. Synth. Catal. 2006, 348, 55.
(c) Lee, D. -Y. ; Kim, I. -J. ; Jun, C. -H. Angew. Chem., Int. Ed. 2002, 41, 3031.
(d) Jun, C. -H. Chem. Soc. Rev. 2004, 33, 610.
(e) Park, Y. G. ; Park, J. -W. ; Jun, C. -H. Acc. Chem. Res. 2008, 41, 222.
Jun, C.-H.; Lee, H. J. Am. Chem. Soc. 1999, 121, 880.
doi: 10.1021/ja983197s
Jun, C.-H.; Lee, D.-Y.; Kim, Y.-H.; Lee, H. Organometallics 2001, 20, 2928.
doi: 10.1021/om010087c
Jun, C.-H.; Lee, H.; Lim, S.-G. J. Am. Chem. Soc. 2001, 123, 751.
doi: 10.1021/ja0033537
Ahn, J. A.; Chang, D. H.; Park, Y. J.; Yon, Y. R.; Loupy, A.; Jun, C H. Adv. Synth. Catal. 2006, 348, 55.
doi: 10.1002/(ISSN)1615-4169
Vautravers, N. R.; Regent, D. D.; Breit, B. Chem. Commun. 2011, 47, 6635.
doi: 10.1039/c1cc10683j
Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.
doi: 10.1021/jo300779q
Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
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
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
Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
Fei Xie , Chengcheng Yuan , Haiyan Tan , Alireza Z. Moshfegh , Bicheng Zhu , Jiaguo Yu . d带中心调控过渡金属单原子负载COF吸附O2的理论计算研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2407013-. doi: 10.3866/PKU.WHXB202407013
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
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
Tiantian MA , Sumei LI , Chengyu ZHANG , Lu XU , Yiyan BAI , Yunlong FU , Wenjuan JI , Haiying YANG . Methyl-functionalized Cd-based metal-organic framework for highly sensitive electrochemical sensing of dopamine. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 725-735. doi: 10.11862/CJIC.20230351
Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
Fugui XI , Du LI , Zhourui YAN , Hui WANG , Junyu XIANG , Zhiyun DONG . Functionalized zirconium metal-organic frameworks for the removal of tetracycline from water. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 683-694. doi: 10.11862/CJIC.20240291
Lubing Qin , Fang Sun , Meiyin Li , Hao Fan , Likai Wang , Qing Tang , Chundong Wang , Zhenghua Tang . 原子精确的(AgPd)27团簇用于硝酸盐电还原制氨:一种配体诱导策略来调控金属核. Acta Physico-Chimica Sinica, 2025, 41(1): 2403008-. doi: 10.3866/PKU.WHXB202403008
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
Xuejiao Wang , Suiying Dong , Kezhen Qi , Vadim Popkov , Xianglin Xiang . Photocatalytic CO2 Reduction by Modified g-C3N4. Acta Physico-Chimica Sinica, 2024, 40(12): 2408005-. doi: 10.3866/PKU.WHXB202408005
Shiyang He , Dandan Chu , Zhixin Pang , Yuhang Du , Jiayi Wang , Yuhong Chen , Yumeng Su , Jianhua Qin , Xiangrong Pan , Zhan Zhou , Jingguo Li , Lufang Ma , Chaoliang Tan . 铂单原子功能化的二维Al-TCPP金属-有机框架纳米片用于增强光动力抗菌治疗. Acta Physico-Chimica Sinica, 2025, 41(5): 100046-. doi: 10.1016/j.actphy.2025.100046
Hailian Tang , Siyuan Chen , Qiaoyun Liu , Guoyi Bai , Botao Qiao , Fei Liu . Stabilized Rh/hydroxyapatite Catalyst for Furfuryl Alcohol Hydrogenation: Application of Oxidative Strong Metal-Support Interactions in Reducing Conditions. Acta Physico-Chimica Sinica, 2025, 41(4): 100036-. doi: 10.3866/PKU.WHXB202408004
Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al2O3催化剂光热催化CO2甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
Tong Zhou , Xue Liu , Liang Zhao , Mingtao Qiao , Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020
Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO4/g-C3N4 S-Scheme Heterojunction with Nitrogen Defect for CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002