Citation: Geng Dianguo. Recent Advances on Transition-Metal-Catalyzed Allenamides Cyclization[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 301-317. doi: 10.6023/cjoc201807028 shu

Recent Advances on Transition-Metal-Catalyzed Allenamides Cyclization

Geng Dianguo ^,

Zibo Vocational Institute, Zibo 255314

Corresponding author: Geng Dianguo, gengdianguo@126.com
Received Date: 17 July 2018
Revised Date: 6 September 2018
Available Online: 26 February 2018

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With the especial reactivity, selectivity, availability and stability, the allenamides have got more and more attention, and the reports on allenamides cyclization grow rapidly. This review gives an up-to-date overview of transition-metal-catalyzed allenamides cyclization, which are sorted by metal catalysts in eight categories of Pd, Ru, Rh, Au, Co, Ag, Pt and Ni. For most of these transformations, the plausible mechanisms are demonstrated in details. Clarification of these issues is the key point for understanding the transition-metal-catalyzed allenamides cyclization and developing new high performance methodologies for chemists.
- allenamides,
- cyclization,
- heterocyclic compounds,
- transition metal catalysis
1. [1]
2. [2]
  Grigg, R. Sridharan, V. Xu, L.-H. J. Chem. Soc., Chem. Commun. 1995, 1903.
3. [3]
  Grigg, R.; Köppen, I.; Rasparini, M.; Sridharan, V. Chem. Commun. 2001, 96.
4. [4]
  Grigg, R.; McCaffrey, S.; Sridharan, V.; Fishwick, C. W. G.; Kilner, C.; Korn, S.; Bailey, K.; Blacker, J. Tetrahedron 2006, 62, 12159. doi: 10.1016/j.tet.2006.09.098
5. [5]
  Inamoto, K.; Yamamoto, A.; Ohsawa, K.; Hiroya, K.; Sakamoto, T. Chem. Pharm. Bull. 2005, 53, 1502. doi: 10.1248/cpb.53.1502
6. [6]
  Husinec, S.; Petkovic, M.; Savic, V.; Simic, M. Synthesis 2012, 44, 399. doi: 10.1055/s-0031-1289658
7. [7]
  Xie, Z.; Wu, P.; Cai, L.; Tong, X. Tetrahedron Lett. 2014, 55, 2160. doi: 10.1016/j.tetlet.2014.02.087
8. [8]
  Yan, F.; Liang, H, ; Song, J.; Cui, J.; Liu, Q.; Liu, S.; Wang, P.; Dong, Y.; Liu, H. Org. Lett. 2017, 19, 86. doi: 10.1021/acs.orglett.6b03364
9. [9]
  Beccalli, E. M.; Bernasconi, A.; Borsini, E.; Broggini, G.; Rigamonti, M.; Zecchi, G. J. Org. Chem. 2010, 75, 6923 doi: 10.1021/jo101501u
10. [10]
  Grigg, R.; Loganathan, V.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1996, 52, 11479. doi: 10.1016/0040-4020(96)00638-2
11. [11]
  Gardiner, M.; Grigg, R.; Sridharan, V.; Vicker, N. Tetrahedron Lett. 1998, 39, 435. doi: 10.1016/S0040-4039(97)10541-X
12. [12]
  Fuwa, H.; Sasaki, M. Org. Biomol. Chem. 2007, 5, 2214. doi: 10.1039/b707338k
13. [13]
  Grigg, R.; Sansano, J. M. Tetrahedron 1996, 52, 13441. doi: 10.1016/0040-4020(96)00801-0
14. [14]
  Parthasarathy, K.; Jeganmohan, M.; Cheng, C. Org. Lett. 2006, 8, 621. doi: 10.1021/ol0527936
15. [15]
  Cao, J.; Kong, Y.; Deng, Y.; Lai, G.; Cui, Y.; Hu, Z.; Wang, G. Org. Biomol. Chem. 2012, 10, 9556. doi: 10.1039/c2ob26727f
16. [16]
  Grigg, R.; Sansano, J. M.; Santhakumar, V.; Sridharan, V.; Thangavelanthum, R.; Thornton-Pett, M.; Wilson, D. Tetrahedron 1997, 53, 11803. doi: 10.1016/S0040-4020(97)00754-0
17. [17]
  Fuwa, H.; Sasaki, M. Org. Biomol. Chem. 2007, 5, 2214. doi: 10.1039/b707338k
18. [18]
  Liang, H.; Yan, F.; Dong, X.; Liu, Q.; Wei, X.; Liu, S.; Dong, Y.; Liu, H. Chem. Commun. 2017, 53, 3138. doi: 10.1039/C7CC00191F
19. [19]
  Zhu, S.; Cao, J.; Wu, L.; Huang, X. J. Org. Chem. 2012, 77, 1049.
20. [20]
  (a) Zhu, C.; Yang, B.; Jiang, T.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2015, 54, 9066.
  (b) Qiu, Y.; Yang, B.; Zhu, C.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2016, 128, 6630.
21. [21]
  Persson, A. K. Å.; Bäckvall, J.-E. Angew. Chem., Int. Ed. 2010, 49, 4624. doi: 10.1002/anie.201000726
22. [22]
  (a) Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. J. Org. Chem. 2006, 71, 4255.
  (b) Donohoe, T. J.; O'Riordan, T. J. C.; Rosa, C. P. Angew. Chem., Int. Ed. 2009, 48, 1014.
23. [23]
  Poeylaut-Palena, A. A.; Testero, S. A.; Mata, E. G. Chem. Commun. 2011, 47, 1565. doi: 10.1039/C0CC04115G
24. [24]
  Edlin, C. D.; Faulkner, J.; Quayle, P. Tetrahedron Lett. 2006, 47, 1145. doi: 10.1016/j.tetlet.2005.12.018
25. [25]
  Bokka, A.; Hua, Y.; Berlin, A. S.; Jeon, J. ACS Catal. 2015, 5, 3189. doi: 10.1021/acscatal.5b00431
26. [26]
  (a) Kim, B. G.; Snapper, M. L. J. Am. Chem. Soc. 2006, 128, 52.
  (b) Peppers, B. P.; Diver, S. T. J. Am. Chem. Soc. 2004, 126, 9524.
27. [27]
  Zeng, X.; Wei, Z.; Farina, V.; Napolitano, E.; Xu, Y.; Zhang, L.; Haddad, N.; Yee, N. K.; Grinberg, N.; Shen, S.; Senanayake, C. H. J. Org. Chem. 2006, 71, 8864. doi: 10.1021/jo061587o
28. [28]
  Dornan, P. K.; Wickens, Z. K.; Grubbs, R. H. Angew. Chem., Int. Ed. 2015, 54, 7134. doi: 10.1002/anie.201501505
29. [29]
  Gavenonis, J.; Arroyo, R. V.; Snapper, M. L. Chem. Commun. 2010, 46, 5692. doi: 10.1039/c0cc00008f
30. [30]
  (a) Rosillo, M.; Casarrubios, L.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2001, 42, 7029.
  (b) Rosillo, M.; Domínguez, G.; Casarrubios, L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084.
31. [31]
  (a) López, F.; Delgado, A.; Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. J. Am. Chem. Soc. 2004, 126, 10262.
  (b) Arisawa, M.; Fujii, Y.; Kato, H.; Fukuda, H.; Matsumoto, T.; Ito, M.; Abe, H.; Ito, Y.; Shuto, S. Angew. Chem., Int. Ed. 2013, 52, 1003.
32. [32]
  Desroy, N.; Robert-Peillard, F.; Toueg, J.; Hénaut, C.; Duboc, R.; Rager, M.-N.; Savignac, M.; Gênet, J.-P. Synthesis 2004, 2665.
33. [33]
  Kinderman, S. S.; Van Maarseveen, J. H.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. T. Org. Lett. 2001, 3, 2045. doi: 10.1021/ol016013e
34. [34]
  Nada, T.; Yoneshige, Y.; Ii, Y.; Matsumoto, T.; Fujioka, H.; Shuto, S.; Arisawa, M. ACS Catal. 2016, 6, 3168. doi: 10.1021/acscatal.6b00628
35. [35]
  Barluenga, J.; Vicente, R.; López, L. A.; Tomás. M. J. Am. Chem. Soc. 2006, 128, 7050.
36. [36]
  Brummond, K. M.; Yan, B. Synlett 2008, 2303.
37. [37]
  Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 1463. doi: 10.1021/ja3099728
38. [38]
  Zheng, W.; Bora, P. P.; Sun, G.; Kang. Q. Org. Lett. 2016, 18, 3694. doi: 10.1021/acs.orglett.6b01731
39. [39]
  Lin, T.; Zhu, C.; Zhang, P.; Wang, Y.; Wu, H.; Feng, J.; Zhang, J. Angew. Chem., Int. Ed. 2016, 55, 10844. doi: 10.1002/anie.201605530
40. [40]
  Hyland, C. J. T.; Hegedus, L. S. J. Org. Chem. 2006, 71, 8658. doi: 10.1021/jo061340r
41. [41]
  Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2007, 9, 4821. doi: 10.1021/ol702179n
42. [42]
  González-Gómez, A.; Domínguez, G.; Pérez-Castells, J. Eur. J. Org. Chem. 2009, 5057.
43. [43]
  Ma, Z.; He, S.; Song, W.; Hsung, R. P. Org. Lett. 2012, 14, 5736. doi: 10.1021/ol302743k
44. [44]
  Li, X.; Zhu, L.; Zhou, W.; Chen. Z. Org. Lett. 2012, 14, 436. doi: 10.1021/ol202703a
45. [45]
  Faustino, H.; Bernal, P.; Castedo, L.; López, F.; Mascareñas, J. L. Adv. Synth. Catal. 2012, 354, 1658. doi: 10.1002/adsc.201200047
46. [46]
  Suarez-Pantiga, S.; Hernández-Díaz, C.; Piedrafita, M.; Rubio, E.; Gonzáleza, J. M. Adv Synth. Catal. 2012, 354, 1651. doi: 10.1002/adsc.201200043
47. [47]
  Ocello, R.; Nisi, A. D.; Jia, M.; Yang, Q.; Monari, M.; Giacinto, P.; Bottoni, A.; Miscione, G. P.; Bandini. M. Chem. Eur. J. 2015, 21, 18445. doi: 10.1002/chem.201503598
48. [48]
  Li, G.; Zhou, E.; Li, X.; Bi, Q.; Wang, Z.; Zhao, Z.; Hu, W.; Chen, Z. Chem. Commun. 2013, 49, 4770. doi: 10.1039/c3cc41769g
49. [49]
  Wang, Y.; Zhang, P.; Qian, D.; Zhang, J. Angew. Chem., Int. Ed. 2015, 54, 14849. doi: 10.1002/anie.201507165
50. [50]
  Singh, R. R.; Pawar, S. K.; Huang, M.; Liu, R. Chem. Commun. 2016, 52, 11434. doi: 10.1039/C6CC04308A
51. [51]
  Faustino, H.; López, F.; Castedo, L.; Mascareñas, J. L. Chem. Sci. 2011, 2, 633. doi: 10.1039/c0sc00630k
52. [52]
  Francos, J.; Grande-Carmona, F.; Faustino, H.; Iglesias-Sigüenza, J.; Díez, E.; Alonso, I.; Fernández, R.; Lassaletta, J. M.; López, F.; Mascareñas, J. L. J. Am. Chem. Soc. 2012, 134, 14322. doi: 10.1021/ja3065446
53. [53]
  Pirovano, V.; Decataldo, L.; Rossi, E.; Vicente, R. Chem. Commun. 2013, 49, 3594. doi: 10.1039/c3cc41514g
54. [54]
  Faustino, H.; Alonso, I.; Mascareñas, J. L.; López, F. Angew. Chem., Int. Ed. 2013, 52, 6526. doi: 10.1002/anie.201302713
55. [55]
  Faustino, H.; Varela, I.; Mascareñas, J. L.; López, F. Chem. Sci. 2015, 6, 2903. doi: 10.1039/C5SC00295H
56. [56]
  Varela, I.; Faustino, H.; Díez, E.; Iglesias-Sigüenza, J.; Grande- Carmona, F.; Fernandez, R.; Lassaletta, J. M.; Mascareñas, J. L.; López. F. ACS Catal. 2017, 7, 2397. doi: 10.1021/acscatal.6b03651
57. [57]
  Peng, S.; Cao, S.; Sun, J. Org. Lett. 2017, 19, 524. doi: 10.1021/acs.orglett.6b03691
58. [58]
  Anorbe, L.; Poblador, A.; Domínguez, G.; Pérez-Castells, J. Tetrahedron Lett. 2004, 45, 4441. doi: 10.1016/j.tetlet.2004.04.061
59. [59]
  Hu, Y.; Yi, R.; Wu, F.; Wan, B. J. Org. Chem. 2013, 78, 7714. doi: 10.1021/jo401330t
60. [60]
  Brioche, J.; Meyer, C.; Cossy, J. Org. Lett. 2013, 15, 1626. doi: 10.1021/ol400402n
61. [61]
  Chakrabarty, I.; Inamdar, S. M.; Akram, M. O.; Gade, A. B.; Banerjee, S.; Berac, S.; Patil, N. T. Chem. Commun. 2017, 53, 196. doi: 10.1039/C6CC07874E
62. [62]
  Liu, R.; Hu, J.; Hong, J.; Lu, C.; Gao, J.; Jia, Y. Chem. Sci. 2017, 8, 2811. doi: 10.1039/C6SC05450A
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