Zinc-catalyzed cyclopropenation of alkynes via 2-furylcarbenoids

Organic Letters

Volumn 16, Issue 21, 2014, Pages 5780-5783

  González, María J ^a   López, Luis A ^a   Vicente, Rubén ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84910022536     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol502848n     Document Type: Article

References (48)

1. Liu, H.-W.; Walsh, C. T. The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; John Wiley & Sons Ltd.: New York, 1987; p 959.
2. Wessjohann, L. A.; Brandt, W.; Thiemann, T. Chem. Rev. 2003, 103, 1625
3. Rademacher, P. Chem. Rev. 2003, 103, 933
4. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
5. Zhu, Z.-B.; Wei, Y.; Shi, M. Chem. Soc. Rev. 2011, 40, 5534
6. Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221
7. Baird, M. S. Chem. Rev. 2003, 103, 1271
8. Phun, L. H.; Aponte-Guzman, J.; France, S. Synlett 2012, 2723
9. Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323
10. Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 7, 3353
11. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977
12. Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1991, 113, 723
13. Denmark, S. E.; Edwards, J. P.; Wilson, S. R. J. Am. Chem. Soc. 1992, 114, 2592
14. Charette, A. B.; Marcoux, J.-F. J. Am. Chem. Soc. 1996, 118, 4539
15. Charette, A. B.; Marcoux, J.-F.; Bélanger-Gariépy, F. J. Am. Chem. Soc. 1996, 118, 6792
16. Charette, A. B.; Marcoux, J.-F.; Molinaro, C.; Beauchemin, A.; Brochu, C.; Isabel, E. J. Am. Chem. Soc. 2000, 122, 4508
17. Vo-Quang, L.; Cadiot, P.; Willemart, A. Compt. Rend. 1962, 255, 950
18. Castellucci, N. T.; Griffin, C. E. J. Am. Chem. Soc. 1960, 82, 4107
19. Jautelat, M.; Schwarz, V. Tetrahedron Lett. 1966, 7, 5101
20. Wittig, G.; Hutchison, J. J. Liebigs Ann. Chem. 1970, 741, 79
21. Wipf, P.; Stephenson, C. R. J.; Okumura, K. J. Am. Chem. Soc. 2003, 125, 14694
22. Briones, J. F.; Davies, H. M. L. J. Am. Chem. Soc. 2012, 134, 11916
23. Briones, J. F.; Hansen, J.; Hardcastle, K. I.; Autschbach, J.; Davies, H. M. L. J. Am. Chem. Soc. 2010, 132, 17211
24. Lindsay, V. N. G.; Fiset, D.; Gritsch, P. J.; Azzi, S.; Charette, A. B. J. Am. Chem. Soc. 2013, 135, 1463
25. Cui, X.; Xu, X.; Lu, H.; Zhu, S.; Wojtas, L.; Zhang, X. P. J. Am. Chem. Soc. 2011, 133, 3304
26. Vicente, R.; González, J.; González, J.; Riesgo, L.; López, L. A. Angew. Chem., Int. Ed. 2012, 51, 8063
27. González, J.; López, L. A.; Vicente, R. Chem. Commun. 2014, 8536
28. Song, B.; Li, L.-H.; Song, X.-R.; Qiu, Y.-F.; Zhong, M.-J.; Zhou, P.-X.; Liang, Y.-M. Chem.-Eur. J. 2014, 20, 5910
29. Enthaler, S. ACS Catal. 2013, 3, 150
30. Wu, X.-F. Chem.-Asian J. 2012, 7, 2502
31. Wu, X.-F.; Neumann, H. Adv. Synth. Catal. 2012, 254, 3141
32. Sniady, A.; Durham, A.; Morreale, M. S.; Wheeler, K. A.; Dembinsky, R. Org. Lett. 2007, 9, 1175
33. Alex, K.; Tillack, A.; Schwarz, N.; Beller, M. Angew. Chem., Int. Ed. 2008, 47, 2304
34. Studte, C.; Breit, B. Angew. Chem., Int. Ed. 2008, 47, 5451
35. Sugiishi, T.; Nakamura, H. J. Am. Chem. Soc. 2012, 134, 2504
36. Nagashima, Y.; Takita, R.; Yoshida, K.; Hirano, K.; Uchiyama, M. J. Am. Chem. Soc. 2013, 135, 18730
37. Hu, F.; Xia, Y.; Ma, C.; Zhang, Y.; Wang, J. Org. Lett. 2014, 16, 4082
38. Xiao, Q.; Xia, Y.; Li, H.; Zhang, Y.; Wang, J. Angew. Chem., Int. Ed. 2011, 50, 1114
39. 2NEt), allene derivatives were not detected, yet significantly lower yields of cyclopropene 3a were observed.
40. The use of rhodium catalysts under otherwise identical reaction conditions leads to a cascade sequence involving the participation of cyclopropenes, which could be isolated only in few cases; see: González, M. J.; López, E.; Vicente, R. Chem. Commun. 2014, 5379
41. Wong, H. N. C.; Hou, X.-L.; Yeung, K.-S.; Huang, H. In Modern Heterocyclic Chemistry; álvarez-Builla, J.; Vaquero, J.-J.; Barluenga, J., Eds.; Wiley-VCH: Meinheim, 2011.
42. Boto, A.; álvarez, L. In Heterocycles in Natural Products Syntheis; Majumdar, K. C.; Chattopdahyay, S. K., Eds.; Wiley-VCH: Meinheim, 2011.
43. Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1997; Vol. 2, p 395. For selected examples of relevant compounds containing furans, see
44. Cui, X.; Xu, X.; Wojtas, L.; Kim, M. M.; Zhang, X. P. J. Am. Chem. Soc. 2012, 134, 19981
45. Woo, C. H.; Beaujuge, P. M.; Holcombe, T. W.; Lee, O. P.; Fréchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 15547
46. Gidron, O.; Diskin-Posner, Y.; Bendikov, M. J. Am. Chem. Soc. 2010, 132, 2148
47. For a silver-catalyzed cyclopropenation of internal alkynes with diazocompounds as the carbene source, see: Briones, J. F.; Davies, H. M. L. Org. Lett. 2011, 13, 3984
48. A similar mechanism has been proposed in the cyclopropenation of terminal alkynes with rhodium carbenoids; see: Nowlan, D. T., III; Singleton, D. A. J. Am. Chem. Soc. 2005, 127, 6190