Palladium-catalyzed esterification-hydroarylation reactions of 2-alkynyl-benzaldehydes with aryl iodides in methanol

Synlett

Volumn , Issue 9, 2004, Pages 1497-1502

  Wei, Li Lan ^a,b   Wei, Li Mei ^b   Pan, Wen Bin ^b   Wu, Ming Jung ^a  

^a KAOHSIUNG MEDICAL UNIVERSITY   (Taiwan)

^b FOOYIN UNIVERSITY   (Taiwan)

Author keywords

2 alkynylbenzaldehydes; Coupling; Esterification hydroarylation; Palladium

Indexed keywords

BENZALDEHYDE DERIVATIVE; BENZOFURAN DERIVATIVE; BENZOIC ACID DERIVATIVE; IODINE DERIVATIVE; METHANOL; PALLADIUM COMPLEX; POTASSIUM DERIVATIVE;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; DEHYDROGENATION; ESTERIFICATION; SUBSTITUTION REACTION;

EID: 3943089020     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829056     Document Type: Article

References (34)

1. Recent reviews: see (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067. (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (d) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
2. Recent reviews: see (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067. (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (d) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
3. Recent reviews: see (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067. (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (d) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
4. Recent reviews: see (a) Cacchi, S. J. Organomet. Chem. 1999, 576, 42. (b) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067. (c) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12. (d) Cacchi, S.; Fabrizi, G.; Goggiomani, A. Heterocycles 2002, 56, 613.
5. Luo, F.-T.; Schreuder, I.; Wang, R.-T. J. Org. Chem. 1992, 57, 2213.
6. (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Synthesis 1986, 749.
7. (b) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Marinelli, F.; Fabrizi, G. J. Org. Chem. 1996, 61, 9280.
8. (a) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915.
9. (b) Luo, F.-T.; Wang, R.-T. Tetrahedron. Lett. 1992, 33, 6835.
10. (c) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.; Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841.
11. (d) Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 63, 1001.
12. (a) Arcadi, A.; Burini, A.; Cacchi, S.; Delmastro, M.; Marinelli, F.; Pietroni, B. R. J. Org. Chem. 1992, 57, 976.
13. (b) Bouyssi, D.; Gore, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett. 1993, 34, 3129.
14. (c) Cavicchioli, M.; Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1996, 37, 1429.
15. (d) Rossi, R.; Bellina, F.; Biagetti, M.; Catanese, A.; Mannina, L. Tetrahedron Lett. 2000, 41, 5281.
16. (a) Fournet, G.; Balme, G.; Van Hemelryck, B.; Gore, J. Tetrahedron Lett. 1990, 31, 5147.
17. (b) Fournet, G.; Balme, G.; Gore, J. Tetrahedron 1991, 47, 6293.
18. (c) Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron Lett. 1991, 32, 6541.
19. (d) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
20. (e) Bruyere, D.; Gaignard, G.; Bouyssi, D.; Balme, G.; Lancelin, J. M. Tetrahedron Lett. 1997, 38, 827.
21. Lin, C.-F.; Lu, W.-D.; Wang, I.-W.; Wu, M.-J. Synlett 2003, 2057.
22. Wei, L.-M.; Lin, C.-F.; Wu, M.-J. Tetrahedron Lett. 2000, 41, 1215.
23. Asao, N.; Nogami, T.; Takahashi, K.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 764.
24. 2O for 5 h gave compound 5a in 82% yield. The 2-alkynylbenzaldehyde 1a was obtained by oxidation of 5a with PCC in 91% yield.
25. 2, final R values[I> 2σ(I)]: R1 = 0.0499, wR2 = 0.1234. Diffractometer: BRUKER SMART APEXCCD. Crystallographic data (excluding structure factors) for this structure have been deposited at the Cambridge Crystallographic Data centre as supplementary publication no. CCDC-223977, and may be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1ED, UK [fax: +44 (1223)336033; e-mail deposit@ccdc.cam.ac.uk].
26. 2, final R values[I > 2σ(I)]: R1 = 0.0902, wR2 = 0.1693. Diffractometer: BRUKER SMART APEXCCD. Crystallographic data (excluding structure factors) for this structure have been deposited at the Cambridge Crystallographic Data center as supplementary publication no. CCDC-231702.
27. Wu, M.-J.; Wei, L.-M.; Lin, C.-F.; Leou, S.-P.; Wei, L.-L. Tetrahedron 2001, 57, 7839.
28. Wei, L.-L.; Wei, L.-M.; Pan, W.-B.; Leou, S.-P.; Wu, M.-J. Tetrahedron Lett. 2003, 44, 1979.
29. Wei, L.-M.; Wei, L.-L.; Pan, W.-B.; Wu, M.-J. Tetrahedron Lett. 2003, 44, 595.
30. (a) Meegalla, S. K.; Taylor, N. J.; Rodrigo, R. J. Org. Chem. 1992, 57, 2422.
31. (b) Larock, R. C.; Doty, M. J. J. Org. Chem. 1993, 58, 4579.
32. (c) Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.
33. (d) Muratake, H.; Nakai, H. Tetrahedron Lett. 1999, 40, 2355.
34. (e) Tanaka, K.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 1607.