Citation: Zhuomin Chi, Yuzhen Gao, Lei Yang, Chunlin Zhou, Meng Zhang, Peiming Cheng, Gang Li. Dearomative spirocyclization via visible-light-induced reductive hydroarylation of non-activated arenes[J]. Chinese Chemical Letters, ;2022, 33(1): 225-228. doi: 10.1016/j.cclet.2021.06.001 shu

Dearomative spirocyclization via visible-light-induced reductive hydroarylation of non-activated arenes

Zhuomin Chi ^{a, b} ,
Yuzhen Gao ^{b, *,} ,
Lei Yang ^b ,
Chunlin Zhou ^b ,
Meng Zhang ^{a, b} ,
Peiming Cheng ^a ,
Gang Li ^{b, *,}

a.
College of Chemistry and Materials Science, Fujian Normal University, Fuzhou 350117, China
b.
Key Laboratory of Coal to Ethylene Glycol and Its Related Technology, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, China

gyz@fjirsm.ac.cn

gangli@fjirsm.ac.cn

Received Date: 15 April 2021
Revised Date: 27 May 2021
Accepted Date: 2 June 2021
Available Online: 9 June 2021

Figures(5)

A visible-light-induced spirocyclizative hydroarylation via reductive dearomatization of a series of non-activated arenes including 2-phenyl indoles and naphthalene derivatives under mild conditions is described. An intriguing chemoselective dearomative hydroarylation of 2-phenyl indoles is presented. This dearomative hydroarylation protocol rapidly delivers valuable spirocycles with carbon−carbon double bonds from readily accessible aromatic precursors in a single step.
- Visible-light-induced,
- Non-activated arene,
- Spirocyclization,
- Dearomatization,
- Reductive hydroarylation
1. [1]
  (a) C.X. Zhuo, W. Zhang, S.L. You, Angew. Chem. Int. Ed. 51 (2012) 12662-12686;
  (b) C. Zheng, S.L. You, Chem 1 (2016) 830-857;
  (c) W.C. Wertjes, E.H. Southgate, D. Sarlah, Chem. Soc. Rev 47 (2018) 7996-8017;
  (d) A.R. Pape, K.P. Kaliappan, E.P. Kündig, Chem. Rev. 100 (2000) 2917-2940.
2. [2]
  (a) Y.S. Cai, Y.W. Guo, K. Krohn, Nat. Prod. Rep. 27 (2010) 1840-1870;
  (b) F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 52 (2009) 6752-6756;
  (c) J.H. Xie, Q.L. Zhou, Acc. Chem. Res. 41 (2008) 581-593.
3. [3]
  (a) Q.F. Wu, H. He, W.B. Liu, S.L. You, J. Am. Chem. Soc. 132 (2010) 11418-11419;
  (b) J. Nan, Z. Zuo, L. Luo, et al., J. Am. Chem. Soc. 135 (2013) 17306-17309;
  (c) C. Shen, R.R. Liu, R.J. Fan, et al., J. Am. Chem. Soc. 137 (2015) 4936-4939;
  (d) X. Li, B. Zhou, R.Z. Yang, et al., J. Am. Chem. Soc. 140 (2018) 13945-13951;
  (e) Z. Zuo, J. Wang, J. Liu, Y. Wang, X. Luan, Angew. Chem. Int. Ed. 59 (2020) 653-657;
  (f) R. Jiang, L. Ding, C. Zheng, S.L. You, Science 371 (2021) 380-386.
4. [4]
  P. Yang, C. Zheng, Y.H. Nie, S.L. You, Chem. Sci. 11(2020) 6830-6835. doi: 10.1039/D0SC02816A
5. [5]
  B. Zhou, H. Wang, Z.Y. Cao, et al., Nat. Commun. 11(2020) 4380-4839. doi: 10.1038/s41467-020-18137-w
6. [6]
  (a) B. Peng, S. Zhang, X. Yu, X. Feng, M. Bao, Org. Lett. 13 (2011) 5402-5405;
  (b) Z.P. Yang, R. Jiang, Q.F. Wu, et al., Angew. Chem. Int. Ed. 57 (2018) 16190-16193;
  (c) T. Ito, S. Harada, H. Homma, et al., J. Am. Chem. Soc. 143 (2021) 604-611;
  (d) M. Chen, X. Wang, Z.H. Ren, Z.H. Guan, CCS Chem. 3 (2021) 69-77.
7. [7]
  (a) M. Okumura, D. Sarlah, Eur. J. Org. Chem. (2020) 1259-1273;
  (b) W.C. Yang, M.M. Zhang, J.G. Feng, Adv. Synth. Catal. 362 (2020) 4446-4461;
  (c) Y. Chen, L.Q. Lu, D.G. Yu, C.J. Zhu, W.J. Xiao, Sci. China Chem. 62 (2018) 24-57;
  (d) Q.Q. Zhou, Y.Q. Zou, L.Q. Lu, W.J. Xiao, Angew. Chem. Int. Ed. 58 (2019) 1586-1604;
  (e) B. Hu, Y. Li, W. Dong, et al., Chem. Commun. 52 (2016) 3709-3712;
  (f) M.J. James, J.L. Schwarz, F. Strieth-Kalthoff, B. Wibbeling, F. Glorius, J. Am. Chem. Soc. 140 (2018) 8624-8628;
  (g) Q. Guo, M. Wang, H. Liu, R. Wang, Z. Xu, Angew. Chem. Int. Ed. 57 (2018) 4747-4751;
  (h) N. Hu, H. Jung, Y. Zheng, et al., Angew. Chem. Int. Ed. 57 (2018) 6242-6246;
  (i) M. Zhu, C. Zheng, X. Zhang, S.L. You, J. Am. Chem. Soc. 141 (2019) 2636-2644;
  (j) M. Zhu, X.L. Huang, H. Xu, et al., CCS Chem 2 (2020) 652-664;
  (k) L. Wu, Y. Hao, Y. Liu, H. Song, Q. Wang, Chem. Commun. 56 (2020) 8436-8439;
  (l) J. Ma, F. Schäfers, C. Daniliuc, et al., Angew. Chem. Int. Ed. 59 (2020) 9639-9645.
8. [8]
  W.J. Zhou, Z.H. Wang, L.L. Liao, et al., Nat. Commun. 11(2020) 3263-3271. doi: 10.1038/s41467-020-17085-9
9. [9]
  A. Chatterjee, B. König, Angew. Chem. Int. Ed. 58(2019) 14289-14294. doi: 10.1002/anie.201905485
10. [10]
  J. Cole, D.F. Chen, M. Kudisch, et al., J. Am. Chem. Soc. 142(2020) 13573-13581. doi: 10.1021/jacs.0c05899
11. [11]
  Y.Z. Cheng, X.L. Huang, W.H. Zhuang, et al., Angew. Chem. Int. Ed. 59(2020) 18062-18067. doi: 10.1002/anie.202008358
12. [12]
  R.C. McAtee, E.A. Noten, C.R.J. Stephenson, Nat. Commun. 11(2020) 2528-2535. doi: 10.1038/s41467-020-16369-4
13. [13]
  Y. Masuda, H. Tsuda, M. Murakami, Angew. Chem. Int. Ed. 60(2021) 3551-3555. doi: 10.1002/anie.202013215
14. [14]
  A.R. Flynn, K. McDaniel, M. Hughes, D. Vogt, N.T. Jui, J. Am. Chem. Soc. 142(2020) 9163-9168. doi: 10.1021/jacs.0c03926
15. [15]
  W. Dai, S.J. Geib, D.P. Curran, J. Am. Chem. Soc. 142(2020) 6261-6267. doi: 10.1021/jacs.0c00490
16. [16]
  E.H. Southgate, J. Pospech, J. Fu, D.R. Holycross, D. Sarlah, Nat. Chem. 8(2016) 922-928. doi: 10.1038/nchem.2594
17. [17]
  S. Stegbauer, C. Jandl, T. Bach, Angew. Chem. Int. Ed. 57(2018) 14593-14596. doi: 10.1002/anie.201808919
18. [18]
  V.K. Soni, H.S. Hwang, Y.K. Moon, et al., J. Am. Chem. Soc. 141(2019) 10538-10545. doi: 10.1021/jacs.9b05572
19. [19]
  W. Dong, Y. Yuan, X. Xie, Z. Zhang, Org. Lett. 22(2020) 528-532. doi: 10.1021/acs.orglett.9b04283
20. [20]
  H. Iwasaki, T. Eguchi, N. Tsutsui, H. Ohno, T. Tanaka, J. Org. Chem. 73(2008) 7145-7152. doi: 10.1021/jo800656a
21. [21]
  Y. Gao, H. Wang, Z. Chi, et al., CCS Chem. 3(2021) 1848-1859.
22. [22]
  E. Speckmeier, T.G. Fischer, K. Zeitler, J. Am. Chem. Soc. 140(2018) 15353-15365. doi: 10.1021/jacs.8b08933
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