Citation: Wu Wen-Ting, Zhang Liming, You Shu-Li. Recent Progress on Gold-catalyzed Dearomatization Reactions[J]. Acta Chimica Sinica, ;2017, 75(5): 419-438. doi: 10.6023/A17020049 shu

Recent Progress on Gold-catalyzed Dearomatization Reactions

Wu Wen-Ting ^a ,
Zhang Liming ^b,*,, ,
You Shu-Li ^a,*,,

a.
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
b.
Department of Chemistry and Biochemistry, University of California, Santa Barbara, California 93106

Corresponding author: Zhang Liming, zhang@chem.ucsb.edu You Shu-Li, slyou@sioc.ac.cn
Received Date: 13 February 2017

Figures(31)

Homogeneous gold catalysis has experienced rapid development since 2004 and generally exhibited high efficiency and good functional group tolerance. On the other hand, catalytic dearomatization reactions provide a unique and straight approach to the construction of highly functionalized molecules with diverse three-dimensional structures from simple aromatic compounds. In this perspective, recent examples on gold-catalyzed dearomatization reactions are summarized in two main categories: gold-catalyzed rearrangements and gold-catalyzed hydrofunctionalizations of alkynes and allenes. In the first category, intra-and inter-molecular dearomatization reactions were achieved via gold-catalyzed rearrangements of propargylic ester and its derivatives. Although this area is still at its early stage, several outstanding asymmetric examples have been reported by Shi and Toste. In the second category, an array of dearomatization reactions via gold-catalyzed hydrofunctionalizations of alkynes and allenes were presented. All these cases have shown great potentials for convenient and straightforward construction of spiro and/or bridged polycyclic molecules, and some of them have exhibited excellent enantioselectivity. In addition, salient features and proposed mechanisms for these two types of reactions are also described.
- gold catalysis,
- dearomatization,
- asymmetric catalysis,
- rearrangement,
- hydrofunctionalization
1. [1]
  Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. doi: 10.1021/ja00280a056
2. [2]
  (a) Teles, J. H.; Brode, S.; Chabanas, M. Angew. Chem., Int. Ed. 1998, 37, 1415; (b) Mizushima, E.; Sato, K.; Hayashi, T.; Tanaka, M. Angew. Chem., Int. Ed. 2002, 41, 4563.
3. [3]
  For recent books: (a) Toste, F. D.; Michelet, V. Gold Catalysis: An Homogeneous Approach, Imperial College Press, London, 2014; (b) Slaughter, L. M. Homogeneous Gold Catalysis, Springer, 2015; (c) Rappoport, Z.; Liebman, J. F.; Marek, I. The Chemistry of Organogold Compounds, Wiley, Chichester, 2014.
4. [4]
  For recent reviews: (a) Hashmi, A. S. K. Acc. Chem. Res. 2014, 47, 864; (b) Yeom, H.-S.; Shin, S. Acc. Chem. Res. 2014, 47, 966; (c) Zhang, L. Acc. Chem. Res. 2014, 47, 877; (d) Wang, Y.-M.; Lackner, A. D.; Toste, F. D. Acc. Chem. Res. 2014, 47, 889; (e) Obradors, C.; Echavarren, A. M. Acc. Chem. Res. 2014, 47, 902; (f) Zhang, D.-H.; Tang, X.-Y.; Shi, M. Acc. Chem. Res. 2014, 47, 913; (g) Yang, W.; Hashmi, A. S. K. Chem. Soc. Rev. 2014, 43, 2941; (h) Xie, J.; Pan, C.; Abdukader, A.; Zhu, C. Chem. Soc. Rev. 2014, 43, 5245; (i) Muratore, M. E.; Homs, A.; Obradors, C.; Echavarren, A. M. Chem. Asian J. 2014, 9, 3066; (j) Inamdar, S. M.; Konala, A.; Patil, N. T. Chem. Commun. 2014, 50, 15124; (k) Obradors, C.; Echavarren, A. M. Chem. Commun. 2014, 50, 16; (l) Gu, P.; Xu, Q.; Shi, M. Tetrahedron Lett. 2014, 55, 577; (m) Qian, D.; Zhang, J. Chem. Soc. Rev. 2015, 44, 677; (n) Joost, M.; Amgoune, A.; Bourissou, D. Angew. Chem., Int. Ed. 2015, 54, 15022; (o) Jia, M.; Bandini, M. ACS Catal. 2015, 5, 1638; (p) Debrouwer, W.; Heugebaert, T. S. A.; Roman, B. I.; Stevens, C. V. Adv. Synth. Catal. 2015, 357, 2975; (q) Goodwin, J. A.; Aponick, A. Chem. Commun. 2015, 51, 8730; (r) Dorel, R.; Echavarren, A. M. J. Org. Chem. 2015, 80, 7321; (s) Ranieri, B.; Escofet, I.; Echavarren, A. M. Org. Biomol. Chem. 2015, 13, 7103; (t) Wei, F.; Song, C.; Ma, Y.; Zhou, L.; Tung, C.-H.; Xu, Z. Sci. Bull. 2015, 60, 1479; (u) Liu, L.; Zhang, J. Chem. Soc. Rev. 2016, 45, 506; (v) Zheng, Z.; Wang, Z.; Wang, Y.; Zhang, L. Chem. Soc. Rev. 2016, 45, 4448; (w) Zi, W.; Dean, T. F. Chem. Soc. Rev. 2016, 45, 4567; (x) Li, Y.; Li, W.; Zhang, J. Chem. Eur. J. 2017, 23, 467.
5. [5]
  (a) Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766; (b) Alcaide, B.; Almendros, P.; Alonso, J. M. Molecules 2011, 16, 7815; (c) Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448; (d) Barbour, P. M.; Marholz, L. J.; Chang, L.; Xu, W.; Wang, X. Chem. Lett. 2014, 43, 572; (e) Fensterbank, L.; Malacria, M. Acc. Chem. Res. 2014, 47, 953; (f) Füerstner, A. Angew. Chem., Int. Ed. 2014, 53, 8587; (g) Füerstner, A. Acc. Chem. Res. 2014, 47, 925; (h) Zhang, Y.; Luo, T.; Yang, Z. Nat. Prod. Rep. 2014, 31, 489; (i) Pflästerer, D.; Hashmi, A. S. K. Chem. Soc. Rev. 2016, 45, 1331.
6. [6]
  Gorin, D. J.; Toste, F. D. Nature 2007, 446, 395. doi: 10.1038/nature05592
7. [7]
8. [8]
9. [9]
  (a) Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994; (b) Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536; (c) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084; (d) Qian, D.; Zhang, J. Chem. Rec. 2014, 14, 280; (e) Wei, Y.; Shi, M. ACS Catal. 2016, 2515.
10. [10]
  Bandini, M. Chem. Soc. Rev. 2011, 40, 1358. doi: 10.1039/C0CS00041H
11. [11]
  Zhang, L. J. Am. Chem. Soc. 2005, 127, 16804. doi: 10.1021/ja056419c
12. [12]
  Yang, J.-M.; Li, P.-H.; Wei, Y.; Tang, X.-Y.; Shi, M. Chem. Commun. 2016, 52, 346. doi: 10.1039/C5CC08381H
13. [13]
  Zi, W.; Wu, H.; Toste, F. D. J. Am. Chem. Soc. 2015, 137, 3225. doi: 10.1021/jacs.5b00613
14. [14]
  Zhang, G.; Huang, X.; Li, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 1814. doi: 10.1021/ja077948e
15. [15]
  Zhang, G.; Zhang, L. J. Am. Chem. Soc. 2008, 130, 12598. doi: 10.1021/ja804690u
16. [16]
  Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916. doi: 10.1021/ja304506g
17. [17]
  Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2014, 16, 3138. doi: 10.1021/ol5012604
18. [18]
  (a) Nevado, C.; Echavarren, A. M. Synthesis 2005, 167; (b) Kitamura, T. Eur. J. Org. Chem. 2009, 2009, 1111; (d) Yamamoto, Y. Chem. Soc. Rev. 2014, 43, 1575.
19. [19]
  Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45, 1105. doi: 10.1002/(ISSN)1521-3773
20. [20]
  Ferrer, C.; Amijs, C. H. M.; Echavarren, A. M. Chem. Eur. J. 2007, 13, 1358. doi: 10.1002/(ISSN)1521-3765
21. [21]
  Zhang, Y.-Q.; Zhu, D.-Y.; Jiao, Z.-W.; Li, B.-S.; Zhang, F.-M.; Tu, Y.-Q.; Bi, Z. Org. Lett. 2011, 13, 3458. doi: 10.1021/ol201194n
22. [22]
  Cheng, B.; Huang, G.; Xu, L.; Xia, Y. Org. Biomol. Chem. 2012, 10, 4417. doi: 10.1039/c2ob25316j
23. [23]
  Xu, W.; Wang, W.; Wang, X. Angew. Chem., Int. Ed. 2015, 54, 9546. doi: 10.1002/anie.v54.33
24. [24]
  Nishiyama, D.; Ohara, A.; Chiba, H.; Kumagai, H.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2016, 18, 1670. doi: 10.1021/acs.orglett.6b00536
25. [25]
  Zhang, L.; Wang, Y.; Yao, Z. J.; Wang, S.; Yu, Z.-X. J. Am. Chem. Soc. 2015, 137, 13290. doi: 10.1021/jacs.5b05971
26. [26]
  Nemoto, T.; Matsuo, N.; Hamada, Y. Adv. Synth. Catal. 2014, 356, 2417. doi: 10.1002/adsc.v356.11/12
27. [27]
  Aparece, M. D.; Vadola, P. A. Org. Lett. 2014, 16, 6008. doi: 10.1021/ol503022h
28. [28]
  Wu, W.-T.; Xu, R.-Q.; Zhang, L.; You, S.-L. Chem. Sci. 2016, 7, 3427. doi: 10.1039/C5SC04130A
29. [29]
  Liu, Y.; Xu, W.; Wang, X. Org. Lett. 2010, 12, 1448. doi: 10.1021/ol100153h
30. [30]
  Noey, E. L.; Wang, X.; Houk, K. N. J. Org. Chem. 2011, 76, 3477. doi: 10.1021/jo200556f
31. [31]
  Podoll, J. D.; Liu, Y.; Chang, L.; Walls, S.; Wang, W.; Wang, X. Proc. Natl. Acad. Sci. U. S. A. 2013, 110, 15573. doi: 10.1073/pnas.1310459110
32. [32]
  Barbour, P. M.; Podoll, J. D.; Marholz, L. J.; Wang, X. Bioorg. Med. Chem. Lett. 2014, 24, 5602. doi: 10.1016/j.bmcl.2014.10.094
33. [33]
  Chang, L.; Podoll, J. D.; Wang, W.; Walls, S.; O'Rourke, C. P.; Wang, X. J. Med. Chem. 2014, 57, 3803. doi: 10.1021/jm500146g
34. [34]
  Barbour, P. M.; Wang, W.; Chang, L.; Pickard, K. L.; Rais, R.; Slusher, B. S.; Wang, X. Adv. Synth. Catal. 2016, 358, 1482. doi: 10.1002/adsc.v358.9
35. [35]
  Cera, G.; Crispino, P.; Monari, M.; Bandini, M. Chem. Commun. 2011, 47, 7803. doi: 10.1039/c1cc12328a
36. [36]
  Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9533. doi: 10.1002/anie.200904388
37. [37]
  Cera, G.; Chiarucci, M.; Bandini, M. Pure Appl. Chem. 2012, 84, 1673.
38. [38]
  Cera, G.; Chiarucci, M.; Mazzanti, A.; Mancinelli, M.; Bandini, M. Org. Lett. 2012, 14, 1350. doi: 10.1021/ol300297t
39. [39]
  Zheng, N.; Chang, Y.-Y.; Zhang, L.-J.; Gong, J.-X.; Yang, Z. Chem. Asian J. 2016, 11, 371. doi: 10.1002/asia.v11.3
40. [40]
  Modha, S. G.; Kumar, A.; Vachhani, D. D.; Jacobs, J.; Sharma, S. K.; Parmar, V. S.; Van Meervelt, L.; Van der Eycken, E. V. Angew. Chem., Int. Ed. 2012, 51, 9572. doi: 10.1002/anie.v51.38
41. [41]
  Modha, S. G.; Vachhani, D. D.; Jacobs, J.; Van Meervelt, L.; Van der Eycken, E. V. Chem. Commun. 2012, 48, 6550. doi: 10.1039/c2cc32586a
42. [42]
  Kumar, A.; Vachhani, D. D.; Modha, S. G.; Sharma, S. K.; Parmar, V. S.; Van der Eycken, E. V. Beilstein J. Org. Chem. 2013, 9, 2097. doi: 10.3762/bjoc.9.246
43. [43]
  Tokimizu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Angew. Chem., Int. Ed. 2015, 54, 7862. doi: 10.1002/anie.201502256
44. [44]
45. [45]
  Shibuya, T.; Noguchi, K.; Tanaka, K. Angew. Chem., Int. Ed. 2012, 51, 6219. doi: 10.1002/anie.201202165
46. [46]
  Oka, J.; Okamoto, R.; Noguchi, K.; Tanaka, K. Org. Lett. 2015, 17, 676. doi: 10.1021/ol503698s
47. [47]
  Baba, T.; Oka, J.; Noguchi, K.; Tanaka, K. Eur. J. Org. Chem. 2015, 2015, 4374. doi: 10.1002/ejoc.201500486
48. [48]
  Jia, M.; Cera, G.; Perrotta, D.; Monari, M.; Bandini, M. Chem. Eur. J. 2014, 20, 9875. doi: 10.1002/chem.201403155
49. [49]
  Shen, Z.-Q.; Li, X.-X.; Shi, J.-W.; Chen, B.-L.; Chen, Z. Tetrahedron Lett. 2015, 56, 4080. doi: 10.1016/j.tetlet.2015.05.021
50. [50]
  Jia, M.; Monari, M.; Yang, Q.-Q.; Bandini, M. Chem. Commun. 2015, 51, 2320. doi: 10.1039/C4CC08736D
51. [51]
  Ocello, R.; De Nisi, A.; Jia, M.; Yang, Q.-Q.; Monari, M.; Giacinto, P.; Bottoni, A.; Miscione, G. P.; Bandini, M. Chem. Eur. J. 2015, 21, 18445. doi: 10.1002/chem.201503598
52. [52]
  Pirovano, V.; Decataldo, L.; Rossi, E.; Vicente, R. Chem. Commun. 2013, 49, 3594. doi: 10.1039/c3cc41514g
53. [53]
  Wang, Y.; Zhang, P.; Liu, Y.; Xia, F.; Zhang, J. Chem. Sci. 2015, 6, 5564. doi: 10.1039/C5SC01827G
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