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
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