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

  • Li Ran ,
  • Xu Xuetao ,
  • Ye Mengchun
Expand
  • 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

Received date: 2020-05-21

  Revised date: 2020-06-10

  Online published: 2020-06-19

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21672107, 21871145, 91856104) and the Department of Education of Guangdong Province (No. 2019KZDXM035).

Abstract

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.

Cite this article

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

References

[1] Sakai, K.; Ide, J.; Oda, O.; Nakamura, N. Tetrahedron Lett. 1972, 1287.
[2] Aloise, A. D.; Layton, M. E.; Shair, M. D. J. Am. Chem. Soc. 2000, 122, 12610.
[3] Sato, Y.; Oonishi, Y.; Mori, M. Angew. Chem., Int. Ed. 2002, 41, 1218.
[4] Crépin, D.; Dawick, J.; Aïssa, C. Angew. Chem., Int. Ed. 2010, 49, 620.
[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.
[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.
[7] Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836.
[8] Shen, Z. M.; Khan, H. A.; Dong, V. M. J. Am. Chem. Soc. 2008, 130, 2916.
[9] Shen, Z. M.; Dornan, P. K.; Khan, H. A.; Woo, T. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 1077.
[10] Coulter, M. M.; Dornan, P. K.; Dong, V. M. J. Am. Chem. Soc. 2009, 131, 6932.
[11] Khan, H. A.; Kou, K. G. M.; Dong, V. M. Chem. Sci. 2011, 2, 407.
[12] Arnold, J. S.; Mwenda, E. T.; Nguyen, H. M. Angew. Chem., Int. Ed. 2014, 53, 3688.
[13] Suggs, J. W. J. Am. Chem. Soc. 1979, 101, 489.
[14] Beletskiy, E. V.; Sudheer, C.; Douglas, C. J. J. Org. Chem. 2012, 77, 5884.
[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] Donets, P. A.; Cramer, N. Angew. Chem., Int. Ed. 2015, 54, 633.
[17] Diesel, J.; Finogenova, A. M.; Cramer, N. J. Am. Chem. Soc. 2018, 140, 4489.
[18] Diesel, J.; Grosheva, D.; Kodama, S.; Cramer, N. Angew. Chem., Int. Ed. 2019, 58, 11044.
[19] Zhang, W. B.; Yang, X. T.; Ma, J. B.; Su, Z. M.; Shi, S. L. J. Am. Chem. Soc. 2019, 141, 5628.
[20] Cai, Y.; Ye, X. D.; Liu, S.; Shi, S. L. Angew. Chem., Int. Ed. 2019, 58, 13433.
[21] Shen, D.; Zhang, W. B.; Li, Z. Y.; Shi, S. L.; Xu, Y. J. Adv. Synth. Catal. 2020, 362, 1125.
Outlines

/

〈 〉