Citation: Sun Xiaoyang, Yu Shouyun. Synthesis of Polysubstituted (Hetero)aromatic Compounds Using Visible-Light-Promoted Radical Triple Bond Insertions[J]. Chinese Journal of Organic Chemistry, ;2016, 36(2): 239-247. doi: 10.6023/cjoc201512006 shu

Synthesis of Polysubstituted (Hetero)aromatic Compounds Using Visible-Light-Promoted Radical Triple Bond Insertions

Sun Xiaoyang ,
Yu Shouyun ^,

1.
State Key Laboratory of Analytical Chemistry for Life Science, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210023

Corresponding author: Yu Shouyun,
Received Date: 3 November 2015
Available Online: 15 December 2015
Fund Project: 国家自然科学基金(No. 21472084)资助项目. (No. 21472084)

Synthesis of polysubstituted (hetero)aromatic compounds enabled by visible-light-promoted radical triple bond insertions has been reviewed. A series of polysubstituted naphthols, furans and isoquinolones were prepared using radical alkyne insertions. 6-Substituted phenanthridine and 1-substituted isoquinoline and pyridine derivatives were synthesized assisted by radical isocyanide insertions. Furthermore, a wide scope of quinoline and quinoxaline derivatives were synthesized assisted by domino radical isocyanide/alkyne insertions and isocyanide/cyano insertions respectively. All reactions could be carried out under visible light photoredox catalysis with good to excellent chemical yields.
- photochemistry,
- radical,
- alkyne,
- isocyanide,
- cyanide,
- aromatic compounds
1. [1]
  [1] (a) Evans, W. C. Nature 1977, 270, 17. (b) Debnath, A. K.; Lopez de Compadre, R. L.; Debnath, G.; Shusterman, A. J.; Hansch, C. J. Med. Chem. 1991, 34, 786. (c) Cornelisse, J.; Havinga, E. Chem. Rev. 1975, 75, 353. (d) Claessens, C. G.; González-Rodríguez, D.; Torres, T. Chem. Rev. 2002, 102, 835. (e) Astruc, D. Tetrahedron 1983, 39, 4027.
2. [2]
  [2] (a) Zeitler, K. Angew. Chem., Int. Ed. 2009, 48, 9785. (b) Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527. (c) Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102. (d) Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687. (e) Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828. (f) Tucker, J. W.; Stephenson, C. R. J. J. Org. Chem. 2012, 77, 1617. (g) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. (h) Hari, D. P.; König, B. Angew. Chem., Int. Ed. 2013, 52, 4734.
3. [3]
  [3] Jiang, H.; Cheng, Y.; Wang, R.; Zheng, M.; Zhang, Y.; Yu, S. Angew. Chem., Int. Ed. 2013, 52, 13289.
4. [4]
  [4] Sun, X.; Yu, S. Org. Lett. 2014, 16, 2938.
5. [5]
  [5] Wang, R.; Jiang, H.; Cheng, Y.; Kadi, A. A.; Fun, H.-K.; Zhang, Y.; Yu, S. Synthesis 2014, 46, 2711.
6. [6]
  [6] Cheng, Y.; Jiang, H.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 5520.
7. [7]
  [7] Jiang, H.; Cheng, Y.; Wang, R.; Zhang, Y.; Yu, S. Chem. Commun. 2014, 50, 6164.
8. [8]
  [8] Cheng, Y.; Yuan, X.; Jiang, H.; Wang, R.; Ma, J.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2014, 356, 2859.
9. [9]
  [9] Tong, K.; Zheng, T.; Zhang, Y.; Yu, S. Adv. Synth. Catal. 2015, 357, 3681.
10. [10]
  [10] Jiang, H.; Cheng, Y.; Zhang, Y.; Yu, S. Org. Lett. 2013, 15, 4884.
11. [11]
  [11] Wang, H.; Yu, S. Org. Lett. 2015, 17, 4272.
12. [12]
  [12] Sun, X.; Li, J.; Ni, Y.; Ren, D.; Hu, Z.; Yu, S. Asian J. Org. Chem. 2014, 3, 1317.
13. [13]
  [13] (a) Zhu, J. Eur. J. Org. Chem. 2003, 1133. (b) van Berkel, S. S.; Bögels, B. G. M.; Wijdeven, M. A.; Westermann, B.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 2012, 3543. (c) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168. (d) Dömling, A. Chem. Rev. 2006, 106, 17.
14. [14]
  [14] (a) Vlaar, T.; Ruijter, E.; Maes, B. U. W.; Orru, R. V. A. Angew. Chem., Int. Ed. 2013, 52, 7084. (b) Qiu, G.; Ding, Q.; Wu, J. Chem. Soc. Rev. 2013, 42, 5257. (c) Lygin, A. V.; de Meijere, A. Angew. Chem., Int. Ed. 2010, 49, 9094. (d) Lang, S. Chem. Soc. Rev. 2013, 42, 4867.
15. [15]
  [15] (a) Zhang, B.; Studer, A. Chem. Soc. Rev. 2015, 44, 3505. (b) Wang, H.; Xu, B. Chin. J. Org. Chem. 2015, 35, 588.
16. [16]
  [16] Other contributions on synthesis of aromatic rings using radical isocynide insertions: (a) Xiao, T.; Li, L.; Lin, G.; Wang, Q.; Zhang, P.; Mao, Z.-W.; Zhou, L. Green Chem. 2014, 16, 2418. (b) He, Z.; Bae, M.; Wu, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2014, 53, 14451. (c) Gu, L.; Jin, C.; Liu, J.; Ding, H.; Fan, B. Chem. Commun. 2014, 50, 4643. (d) Fu, W.; Zhu, M.; Xu, C.; Zou, G.; Wang, Z.; Ji, B. J. Fluorine Chem. 2014, 168, 50.
17. [17]
  [17] Other contributions on synthesis of 6-trifluoromethylated phenanthridines using radical isocynide insertions: (a) Zhang, B.; Studer, A. Org. Lett. 2014, 16, 3990. (b) Zhang, B.; Mück-Lichtenfeld, C.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2013, 52, 10792. (c) Wang, Q.; Dong, X.; Xiao, T.; Zhou, L. Org. Lett. 2013, 15, 4846.
18. [18]
  [18] Other contributions to synthesis of 6-arylphenanthridines using radical isocynide insertions: (a) Xia, Z.; Huang, J.; He, Y.; Zhao, J.; Lei, J.; Zhu, Q. Org. Lett. 2014, 16, 2546. (b) Tobisu, M.; Koh, K.; Furukawa, T.; Chatani, N. Angew. Chem., Int. Ed. 2012, 51, 11363.
19. [19]
  [19] Suzuki, M.; Nunami, K-I.; Matsumoto, K.; Yoneda, N.; Kasuga, O.; Yoshida, H.; Yamaguchi, T. Chem. Pharm. Bull. 1980, 28, 2374.
20. [20]
  [20] Other contributions on synthesis of isoquinolines using vinyl isocyanides insertions: (a) Zhang, B.; Studer, A. Org. Biomol. Chem. 2014, 12, 9895. (b) Wang, H.; Yu, Y.; Hong, X.; Xu, B. Chem. Commun. 2014, 50, 13485. (c) Qian, P.; Du, B.; Zhou, J.; Mei, H.; Han, J.; Pan, Y. RSC Adv. 2015, 5, 64961.
21. [21]
  [21] Other contributions to visible-light-promoted radical alkyne insertions: (a) Yetiskin, O.; Dadashi-Silab, S.; Khan, S. B.; Asiri, A. M.; Yagci, Y. Asian J. Org. Chem. 2015, 4, 442. (b) Tsuchii, K.; Doi, M.; Hirao, T.; Ogawa, A. Angew. Chem., Int. Ed. 2003, 42, 3490. (c) Dong, X.; Xu, Y.; Liu, J. J.; Hu, Y.; Xiao, T.; Zhou, L. Chem.-Eur. J. 2013, 19, 16928.
22. [22]
  [22] Other contributions on domino radical isocyanide/alkyne insertions: (a) Josien, H.; Ko, S.-B.; Bom, D.; Curran, D. P. Chem.-Eur. J. 1998, 4, 67. (b) Josien, H.; Curran, D. P. Tetrahedron 1997, 53, 8881. (c) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385. (d) Curran, D. P.; Liu, H. J. Am. Chem. Soc. 1992, 114, 5863. (e) Curran, D. P.; Du, W. Org. Lett. 2002, 4, 3215. (f) Nanni, D.; Pareschi, P.; Tundo, A. Tetrahedron Lett. 1996, 37, 9337.
23. [23]
  [23] Other contributions on domino radical isocyanide/cyanide insertions: (a) Nanni, D.; Pareschi, P.; Rizzoli, C.; Sgarabotto, P.; Tundo, A. Tetrahedron 1995, 51, 9045. (b) Camaggi, C. M.; Leardini, R.; Nanni, D.; Zanardi, G. Tetrahedron 1998, 54, 5587.
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