Regioselective synthesis of 4,6,7-trisubstituted benzofurans from furfural imines and nonheteroatom stabilized alkynylcarbene complexes

Journal of the American Chemical Society

Volumn 131, Issue 41, 2009, Pages 14628-14629

  Barluenga, José ^a   Gómez, Aránzazu ^a   Santamaría, Javier ^a   Tomás, Miguel ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ARENE RINGS; BENZOFURANS; CARBOCYCLIZATION REACTIONS; CHEMICAL EQUATIONS; GOOD YIELD; IN-SITU; REGIO-SELECTIVE; REGIOSELECTIVE SYNTHESIS;

ALDEHYDES; CHEMICAL REACTIONS; CHROMIUM;

CHROMIUM COMPOUNDS;

4,6,7 BENZOFURAN DERIVATIVE; ALKYNYL GROUP; BENZOFURAN DERIVATIVE; CARBENOID; FURFURAL; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 70350070380     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9063712     Document Type: Article

References (41)

1. Fischer, E. O.; Maasböl, A. Angew. Chem. 1964, 76, 645.
2. Selected reviews: (a) De Meijere, A.; Schirmer, H.; Duetsch, M. Angew. Chem., Int. Ed. 2000, 39, 3964.
3. (b) Herndon, J. W. Tetrahedron 2000, 56, 1257.
4. (c) Barluenga, J.; Santamaría, J.; Tomás, M. Chem. Rev. 2004, 104, 2259.
5. (d) Barluenga, J.; Fernández-Rodríguez, M. A.; Aguilar, E. J. Organomet. Chem. 2005, 690, 539.
6. (e) Gómez-Gallego, M.; Mancheño, M. J.; Sierra, M. A. Acc. Chem. Res. 2005, 38, 44.
7. (f) Herndon, J. W. Coord. Chem. Rev. 2009, 253, 86.
8. (g) Santamaría, J. Curr. Org. Chem. 2009, 13, 31.
9. (h) Metal Carbenes in Organic Synthesis; Dötz, K. H., Ed.; Topics in Organometallic Chemistry; John Wiley & Sons: New York, 2004; Vol.13.
10. Casey, C. P.; Burkhardt, T. J. J. Am. Chem. Soc. 1973, 95, 5833.
11. (a) Casey, C. P.; Burkhardt, T. J.; Bunnell, C. A.; Calabrese, J. C. J. Am. Chem. Soc. 1977, 99, 2127.
12. (b) Casey, C. P.; Polichnowski, S. W. J. Am. Chem. Soc. 1977, 99, 6097.
13. (c) Casey, C. P.; Polichnowski, S. W.; Tuinstra, H. E.; Albin, L. D.; Calabrese, J. C. Inorg. Chem. 1978, 17, 3045.
14. (d) Iwasawa, N.; Maeyama, K.; Saitou, M. J. Am. Chem. Soc. 1997, 119, 1486.
15. For previous studies on Cα-H nonheteroatom stabilized carbene complexes in our group, see: Barluenga, J.; Ballesteros, A.; Bernardo de la Rúa, R.; Santamaría, J.; Rubio, E.; Tomás, M. J. Am. Chem. Soc. 2003, 125, 1834.
16. (a) Barluenga, J.; de Sáa, D.; Gómez, A.; Ballesteros, A.; Santamaría, J.; de Prado, A.; Tomás, M.; Suárez-Sobrino, A. L. Angew. Chem., Int. Ed. 2008, 47, 6225.
17. For dimerizations involving group 7 carbene complexes, see: (b) Casey, C. P.; Kraft, S.; Powell, D. R. J. Am. Chem. Soc. 2000, 122, 3771.
18. (c) Casey, C. P.; Kraft, S.; Powell, D. R. J. Am. Chem. Soc. 2002, 124, 2584.
19. (d) Casey, C. P.; Dzwiniel, T. L. Organometallics 2003, 22, 5285.
20. (e) Casey, C. P.; Dzwiniel, T. L.; Kraft, S.; Guzei, I. A. Organometallics 2003, 22, 3915.
21. (f) Ortin, Y.; Sournia-Saquet, A.; Lugan, N.; Mathieu, R. Chem. Commun. 2003, 1060.
22. Barluenga, J.; García-García, P.; de Sáa, D.; Fernández-Rodríguez, M. A.; Bernardo de la Rúa, R.; Ballesteros, A.; Aguilar, E.; Tomás, M. Angew. Chem., Int. Ed. 2007, 46, 2610.
23. Furfural itself fails to react with complexes 3 up to room temperature. At that temperature Cα-H insertion into THF along with decomposition of 3 was observed.
24. For recent examples, see: (a) Ghosh, S. K.; Buchanan, G. S.; Long, Q. A.; Wei, Y.; Al-Rashid, Z. F.; Skelenicka, H. M.; Hsung, R. P. Tetrahedron 2008, 64, 883.
25. (b) Hussain, I.; Nguyen, V. T. H.; Yawer, M. A.; Dang, T. T.; Fischer, C.; Reinke, H.; Langer, P. J. Org. Chem. 2007, 72, 6255.
26. (c) For a review, see: Feist, H.; Langer, P. Synthesis 2007, 327.
27. The structure of 5 was established by 1D- and 2D-NMR experiments.
28. Appropriately, N-substituted 7-aminobenzofurans have been reported as antitumoral agents. See: (a) Lambert, C. M. P.; Ple, P. PCT Int. Appl 2002030924.
29. (b) Hennequin, L. F. A.; Gibson, K. H.; Foote, K. M. PCT Int. Appl. 2003047583.
30. (c) Hennequin, L. F. A. PCT Int. Appl. 2004041811.
31. We have already experienced the preference of tungsten over chromium for the conjugate addition to alkynyl(methoxy)carbene complexes. See: (a) Barluenga, J.; Tomás, M.; Rubio, E.; López-Pelegrín, J. A.; García-Granda, S.; Pertierra, P. J. Am. Chem. Soc. 1996, 118, 695.
32. (b) Barluenga, J.; Tomás, M.; López-Pelegrín, J. A.; Rubio, E. Tetrahedron Lett. 1997, 38, 3981.
33. For selected examples, see: (a) Kraus, G. A.; Zhang, N.; Verkade, J. G.; Nagarajan, M.; Kisanga, P. B. Org. Lett. 2000, 2, 2409.
34. (b) Knölker, H. J.; Krahl, M. P. Synlett 2004, 528.
35. (c) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292.
36. (d) Carril, M.; San Martín, R.; Tellitu, I.; Domínguez, E. Org. Lett. 2006, 8, 1467.
37. (e) Okitsu, T.; Nakazawa, D.; Taniguchi, R.; Wada, A. Org. Lett. 2008, 10, 4967.
38. Some benzofuran syntheses of limited generality involving the construction of the arene ring have been reported. (a) Dötz, K. H.; Dietz, R. Chem. Ber. 1978, 111, 2517.
39. (b) Wulff, W. D.; McCallum, J. S.; Kunng, F. A. J. Am. Chem. Soc. 1988, 110, 7419.
40. (c) Barluenga, J.; Tomás, M.; Rubio, E.; López- Pelegrín, J. A.; García-Granda, S.; Pérez-Priede, M. J. Am. Chem. Soc. 1999, 121, 3065.
41. (d) Zhang, Y.; Candelaria, D.; Herndon, J. W. Tetrahedron Lett. 2005, 46, 2211.