Citation: Li Ran, Xu Xuetao, Ye Mengchun. Construction of Medium Rings via Transition Metal-Catalyzed Insertion of π-Unsaturated Compounds into C—H Bonds[J]. Chinese Journal of Organic Chemistry, ;2020, 40(10): 3196-3202. doi: 10.6023/cjoc202005056 shu

Construction of Medium Rings via Transition Metal-Catalyzed Insertion of π-Unsaturated Compounds into C—H Bonds

Li Ran ^a,b ,
Xu Xuetao ^a,, ,
Ye Mengchun ^a,b,,

a.
School of Biotechnology and Health Science, Wuyi University, Jiangmen, Guangdong 529020
b.
State Key Laboratory and Institute of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Corresponding author: Xu Xuetao, wyuchemxxt@126.com Ye Mengchun, mcye@nankai.edu.cn
Received Date: 21 May 2020
Revised Date: 10 June 2020
Available Online: 19 June 2020
Fund Project: National Natural Science Foundation of China 21871145National Natural Science Foundation of China 91856104National Natural Science Foundation of China 21672107Department of Education of Guangdong Province 2019KZDXM035Project supported by the National Natural Science Foundation of China (Nos. 21672107, 21871145, 91856104) and the Department of Education of Guangdong Province (No. 2019KZDXM035)

Figures(17)

Medium rings (7~9 membered) widely exist in a variety of natural products that often have important bio-activities, thereby the development of economical and highly efficient synthetic routes to them has received intensive attention. Recent advances on transition metal-catalyzed π-unsaturated compounds inserting into C-H bonds for the construction of medium rings are summarized. According to different strategies that were used to stabilize organometallic intermediates, these methods can be divided into four types, and each of which was described from various aspects including its progress, characteristics, reaction types and mechanisms.
- medium-ring compound,
- transition metal catalysis,
- π-unsaturated bond,
- C-H bond
1. [1]
  Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287.
2. [2]
  Aloise, A. D.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 12610. doi: 10.1021/ja0055920
3. [3]
  Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218. doi: 10.1002/1521-3773(20020402)41:7<1218::AID-ANIE1218>3.0.CO;2-D
4. [4]
  Crépin, D.; Dawick, J.; Aïssa, C. Angew. Chem., Int. Ed. 2010, 49, 620. doi: 10.1002/anie.200904527
5. [5]
  Bendorf, H. D.; Colella, C. M.; Dixon, E. C.; Marchetti, M.; Matukonis, A. N.; Musselman, J. D.; Tiley, T. A. Tetrahedron Lett. 2002, 43, 7031. doi: 10.1016/S0040-4039(02)01552-6
6. [6]
  Bendorf, H. D.; Ruhl, K. E.; Shurer, A. J.; Shaffer, J. B.; Duffin, T. O.; LaBarte, T. L.; Maddock, M. L.; Wheeler, O. W. Tetrahedron Lett. 2012, 53, 1275. doi: 10.1016/j.tetlet.2011.12.125
7. [7]
  Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836. doi: 10.1021/ja0746316
8. [8]
  Shen, Z. M.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916. doi: 10.1021/ja7109025
9. [9]
  Shen, Z. M.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077. doi: 10.1021/ja806758m
10. [10]
  Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932. doi: 10.1021/ja901915u
11. [11]
  Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407. doi: 10.1039/C0SC00469C
12. [12]
  Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angew. Chem., Int. Ed. 2014, 53, 3688. doi: 10.1002/anie.201310354
13. [13]
  Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489. doi: 10.1021/ja00496a040
14. [14]
  Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884. doi: 10.1021/jo300779q
15. [15]
  (a) Ding, Z.; Yoshikai, N. Angew. Chem., Int. Ed. 2013, 52, 8574.
  (b) Donets, P. A.; Cramer, N. J. Am. Chem. Soc. 2013, 135, 11772.
16. [16]
  Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 633.
17. [17]
  Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489. doi: 10.1021/jacs.8b01181
18. [18]
  Diesel, J.; Grosheva, D.; Kodama, S.; Cramer, N. Angew. Chem., Int. Ed. 2019, 58, 11044. doi: 10.1002/anie.201904774
19. [19]
  Zhang, W. B.; Yang, X. T.; Ma, J. B.; Su, Z. M.; Shi, S. L. J. Am. Chem. Soc. 2019, 141, 5628. doi: 10.1021/jacs.9b00931
20. [20]
  Cai, Y.; Ye, X. D.; Liu, S.; Shi, S. L. Angew. Chem., Int. Ed. 2019, 58, 13433. doi: 10.1002/anie.201907387
21. [21]
  Shen, D.; Zhang, W. B.; Li, Z. Y.; Shi, S. L.; Xu, Y. J. Adv. Synth. Catal. 2020, 362, 1125. doi: 10.1002/adsc.201901582
1. [1]
  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
2. [2]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
3. [3]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  Lijuan Liu , Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060
8. [8]
  Pengzi Wang , Wenjing Xiao , Jiarong Chen . Copper-Catalyzed C―O Bond Formation by Kharasch-Sosnovsky-Type Reaction. University Chemistry, 2025, 40(4): 239-244. doi: 10.12461/PKU.DXHX202406090
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  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
14. [14]
  Rui Li , Jiayu Zhang , Anyang Li . Two Levels of Understanding of Chemical Bonds: a Case of the Bonding Model of Hypervalent Molecules. University Chemistry, 2024, 39(2): 392-398. doi: 10.3866/PKU.DXHX202308051
15. [15]
  Linhan Tian , Changsheng Lu . Discussion on Sextuple Bonding in Diatomic Motifs of Chromium Family Elements. University Chemistry, 2024, 39(8): 395-402. doi: 10.3866/PKU.DXHX202401056
16. [16]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
17. [17]
  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
18. [18]
  Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
19. [19]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(9)
Abstract views(1653)
HTML views(258)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142