N-heterocyclic carbene-catalyzed cascade reaction involving the hydroacylation of unactivated alkynes

Journal of the American Chemical Society

Volumn 132, Issue 17, 2010, Pages 5970-5971

  Biju, Akkattu T ^a   Wurz, Nathalie E ^a   Glorius, Frank ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CASCADE REACTIONS; DIKETONES; HYDROACYLATION; N-HETEROCYCLIC CARBENES; STETTER REACTION; UNSATURATED KETONES;

ACETYLENE; CARBON INORGANIC COMPOUNDS; KETONES;

REACTION KINETICS;

ALKYNE DERIVATIVE; CARBENOID; HETEROCYCLIC COMPOUND;

ACYLATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ONE POT SYNTHESIS;

EID: 77951673787     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja102130s     Document Type: Article

References (53)

1. For an excellent review, see: Willis, M. C. Chem. Rev. 2010, 110, 725
2. Stetter, H. and Schreckenberg, M. Angew. Chem., Int. Ed. Engl. 1973, 12, 81
3. Stetter, H. and Kuhlmann, H. Angew. Chem., Int. Ed. Engl. 1974, 13, 539
4. For reviews of NHC organocatalysis, see: Nair, V., Vellalath, S., and Babu, B. P. Chem. Soc. Rev. 2008, 37, 2691
5. Enders, D., Niemeier, O., and Henseler, A. Chem. Rev. 2007, 107, 5606
6. Marion, N., Díez-González, S., and Nolan, S. P. Angew. Chem., Int. Ed. 2007, 46, 2988
7. Phillips, E. M., Chan, A., and Scheidt, K. A. Aldrichimica Acta 2009, 42, 55
8. He, J., Tang, S., Liu, J., Su, Y., Pan, X., and She, X. Tetrahedron 2008, 64, 8797 For hydroacylation of nitriles, see:
9. Vedachalam, S., Zeng, J., Gorityala, B. K., Antonio, M., and Liu, X.-W. Org. Lett. 2010, 12, 352
10. Hirano, K., Biju, A. T., Piel, I., and Glorius, F. J. Am. Chem. Soc. 2009, 131, 14190
11. For selected papers, see: Jun, C.-H., Lee, H., Hong, J.-B., and Kwon, B.-I. Angew. Chem., Int. Ed. 2002, 41, 2146
12. Tanaka, K. and Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492
13. Tsuda, T., Kiyoi, T., and Saegusa, T. J. Org. Chem. 1990, 55, 2554 For a related gold-catalyzed hydroacylation, see:
14. Skouta, R. and Li, C.-J. Angew. Chem., Int. Ed. 2007, 46, 1117
15. Lebeuf, R., Hirano, K., and Glorius, F. Org. Lett. 2008, 10, 4243
16. Hirano, K., Piel, I., and Glorius, F. Adv. Synth. Catal. 2008, 350, 984
17. See the Supporting Information for details.
18. For a mechanistic discussion of related processes, see: Roveda, J.-G., Clavette, C., Hunt, A. D., Gorelsky, S. I., Whipp, C. J., and Beauchemin, A. M. J. Am. Chem. Soc. 2009, 131, 8740
19. Moran, J., Gorelsky, S. I., Dimitrijevic, E., Lebrun, M.-E., Bédard, A.-C., Séguin, C., and Beauchemin, A. M. J. Am. Chem. Soc. 2008, 130, 17893
20. Breslow, R. J. Am. Chem. Soc. 1958, 80, 3719
21. For reviews, see: MacMillan, D. W. C. and Walji, A. M. Synlett 2007, 1477
22. Chapman, C. J. and Frost, C. G. Synthesis 2007, 1
23. Wasilke, J.-C., Obrey, S. J., Baker, R. T., and Bazan, G. C. Chem. Rev. 2005, 105, 1001
24. Ajamian, A. and Gleason, J. L. Angew. Chem., Int. Ed. 2004, 43, 3754
25. Bruggink, A., Schoevaart, R., and Kieboom, T. Org. Process Res. Dev. 2003, 7, 622
26. Nicolaou, K. C., Edmonds, D. J., and Bulger, P. G. Angew. Chem., Int. Ed. 2006, 45, 7134
27. For reviews, see: Yu, X. and Wang, W. Org. Biomol. Chem. 2008, 6, 2037
28. Enders, D., Grondal, C., and Hüttl, M. R. M. Angew. Chem., Int. Ed. 2007, 46, 1570 For selected examples, see: Jiang, H., Elsner, P., Jensen, K. L., Falcicchio, A., Marcos, V., and Jørgensen, K. A. Angew. Chem., Int. Ed. 2009, 48, 6844
29. Simmons, B., Walji, A. M., and MacMillan, D. W. C. Angew. Chem., Int. Ed. 2009, 48, 4349
30. Ishikawa, H., Suzuki, T., and Hayashi, Y. Angew. Chem., Int. Ed. 2009, 48, 1304
31. Wang, J., Li, H., Xie, H.-X., Zu, L.-S., Shen, X., and Wang, W. Angew. Chem., Int. Ed. 2007, 46, 9050
32. Enders, D., Hüttl, M. R. M., Grondal, C., and Raabe, G. Nature 2006, 441, 861
33. For selected examples of benzoin reactions, see: Enders, D. and Kallfass, U. Angew. Chem., Int. Ed. 2002, 41, 1743
34. Enders, D., Niemeier, O., and Balensiefer, T. Angew. Chem., Int. Ed. 2006, 45, 1463
35. Takikawa, H., Hachisu, Y., Bode, J. W., and Suzuki, K. Angew. Chem., Int. Ed. 2006, 45, 3492
36. White, M. J. and Leeper, F. J. J. Org. Chem. 2001, 66, 5124 For reviews of the Stetter reaction, see:
37. Read De Alaniz, J. and Rovis, T. Synlett 2009, 1189
38. Christmann, M. Angew. Chem., Int. Ed. 2005, 44, 2632 Also see:
39. Read De Alaniz, J., Kerr, M. S., Moore, J. L., and Rovis, T. J. Org. Chem. 2008, 73, 2033
40. Enders, D., Breuer, K., and Runsink, J. Helv. Chim. Acta 1996, 79, 1899 For selected work in homoenolate chemistry, see:
41. Burstein, C. and Glorius, F. Angew. Chem., Int. Ed. 2004, 43, 6205
42. Sohn, S. S., Rosen, E. L., and Bode, J. W. J. Am. Chem. Soc. 2004, 126, 14370
43. He, M. and Bode, J. W. Org. Lett. 2005, 7, 3131
44. Nair, V., Vellalath, S., Poonoth, M., and Suresh, E. J. Am. Chem. Soc. 2006, 128, 8736
45. Burstein, C., Tschan, S., Xie, X., and Glorius, F. Synthesis 2006, 2418
46. Chan, A. and Scheidt, K. A. J. Am. Chem. Soc. 2007, 129, 5334
47. Phillips, E. M., Reynolds, T. E., and Scheidt, K. A. J. Am. Chem. Soc. 2008, 130, 2416
48. For the application of NHCs in cascade catalysis, see: Lathrop, S. P. and Rovis, T. J. Am. Chem. Soc. 2009, 131, 13628
49. Ye, W., Cai, G., Zhuang, Z., Jia, X., and Zhai, H. Org. Lett. 2005, 7, 3769
50. Stetter, H. and Kuhlmann, H. Org. React. 1991, 40, 407
51. Treatment of 4a with the carbene generated from 3 resulted in the formation of chromanone 4a′ in 86% yield, presumably by the addition of second molecule of 4a to the intermediate enone. For a related report, see: Stetter, H. and Bender, H.-J. Angew. Chem., Int. Ed. Engl. 1978, 17, 131
52. For the addition of aldehydes to activated alkynes using stoichiometric amounts of NHC, see: Ma, C. and Yang, Y. Org. Lett. 2005, 7, 1343
53. Ma, C., Ding, H., Wu, G., and Yang, Y. J. Org. Chem. 2005, 70, 8919