Cross-coupling reactions of aryl chlorides and bromides with phenyltrimthoxysilane catalyzed by palladium-phosphinous acid complexes

Synthesis

Volumn , Issue 13, 2003, Pages 2069-2073

  Wolf, Christian ^a   Lerebours, Rachel ^a   Tanzini, Elizabeth H ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

Aryl halides; Biaryls; Cross coupling reaction; Palladium phosphinous acid complexes; Phenyltrimethoxysilane

Indexed keywords

COMPLEXATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CROSS COUPLING REACTIONS;

ORGANOMETALLICS;

2 PROPANOL; 4,7 DICHLOROQUINOLINE; 7 CHLORO 4 PHENYLQUINOLINE; ACETIC ACID ETHYL ESTER; ACETONITRILE; ANTIMALARIAL AGENT; BROMINE DERIVATIVE; CHLORINE DERIVATIVE; ESTER DERIVATIVE; HALIDE; KETONE; NITRILE; PALLADIUM; PHENYLTRIMETHOXYSILANE; PHOSPHINE DERIVATIVE; QUINOLINE DERIVATIVE; SILANE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; DRUG SYNTHESIS; ELIMINATION REACTION; REDUCTION; STEREOCHEMISTRY;

EID: 0141618313     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-41018     Document Type: Article

References (50)

1. For a recent review: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
2. (a) Meyer, G.; Rollin, Y.; Perichon, J. Tetrahedron Lett. 1986, 27, 3497.
3. (b) Yang, S. H.; Li, C. S.; Cheng, C. H. J. Org. Chem. 1987, 52, 691.
4. (c) Bozell, J. J.; Vogt, C. E. J. Am. Chem. Soc. 1988, 110, 2655.
5. (d) Merkushev, E. B. Synthesis 1988, 923.
6. (e) Barluenga, J.; Gonzalez, J. M.; Garcia-Martin, M. A.; Campos, P. J.; Asensio, G. J. Org. Chem. 1993, 58, 2058.
7. (f) Milne, J. E.; Jarowicki, K.; Kocienski, P. J. Synlett 2002, 607.
8. (g) Schlosser, M.; Cottet, F. Eur. J. Org. Chem. 2002, 4181.
9. (h) Klapars, A.; Buchwald, S. L. J. Am. Chem, Soc. 2002, 124, 14844.
10. (a) Riermeier, T. H.; Zapf, A.; Beller, M. Top, Catal. 1997, 4, 301.
11. (b) Shirakawa, E.; Yamasaki, K.; Hiyama, T. Synthesis 1998, 1544.
12. (c) Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10.
13. (d) Suzuki, A. J. Organamet. Chem. 1999, 576, 147.
14. (e) Shiota, T.; Yamamori, T. J. Org. Chem. 1999, 64, 453.
15. (f) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1999, 38, 2411.
16. (g) Zhang, C. M.; Huang, J. K.; Trudell, M. L.; Nolan, M. L. J. Org. Chem. 1999, 64, 3804.
17. (h) Bei, X.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855.
18. (i) Bei, X.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. J. Org. Chem. 1999, 64, 6797.
19. (j) Wolfe, J.P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
20. (k) Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
21. (l) Bohm, V. P. W.; Herrmann, W. A. Chem.-Eur. J. 2000, 6, 1017.
22. (m) Gruber, A. S.; Zim, D.; Ebeling, G.; Monteiro, A. I.; Dupont, J. Org. Lett. 2000, 2, 1287.
23. (n) Morales-Morales, D.; Redon, R.; Yung, C.; Jensen, C. M. Chem. Commun. 2000, 1619.
24. (o) Bohm, V. P. W.; Weskamp, T.; Gstottmayr, C. W. K.; Herrmann, W. A. Angew. Chem. Int. Ed. 2000, 39, 1602.
25. (p) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
26. (q) Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
27. (r) Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem., Int. Ed. 2000, 39, 4153.
28. (s) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677.
29. (t) Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
30. Littke, A. F.; Fu, G. C. J. Am. Chem. Sac. 2001, 123, 6989.
31. (v) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
32. (w) Yin, J. J.; Rainka, M. P.; Zhang, X. X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162.
33. (x) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Chem. Commun. 2002, 2608.
34. (y) Bedford, R. B.; Cazin, C. S. J.; Hazelwood, S. L. Chem. Commun. 2002, 2610.
35. (a) Brescia, M.-R.; DeShong, P. J. Org. Chem. 1998, 63, 3156.
36. (b) Mowery, M. E.; DeShong, P. J. Org. Chem. 1999, 64, 1684.
37. (c) Mowery, M. E.; DeShong, P. Org. Lett. 1999, 1, 2137.
38. (d) DeShong, P.; Handy, C. J.; Mowery, M. E. Pure Appl. Chem. 2000, 72, 1655.
39. (e) Correia, R.; DeShong, P. J. Org. Chem. 2001, 66, 7159.
40. (f) Hoke, M. E.; Brescia, M.-R.; Bogaczyk, S.; DeShong, P.; King, B. W.; Crimmins, M. T. J. Org. Chem. 2002, 67, 327.
41. (a) Li, G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
42. (b) Li,G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
43. (c) Li, G. Y. J. Org. Chem. 2002, 67, 3643.
44. We observed significant formation of biquinaldine and biphenyl using POPd and POPd2.
45. Employing aryl halides exhibiting nitro, alcohol, phenol or carboxylic acid groups in the POPd1-catalyzed coupling reaction with phenyltrimethoxysilane did not afford the desired products.
46. El Sayed, K.; Al-Said, M. S.; El-Feraly, F. S.; Ross, S. A. J. Nat. Prod. 2000, 63, 995.
47. (a) O'Neill, P. M.; Bray, P. G.; Hawley, S. R.; Ward, S. A.; Park, B. K. Pharmacol. Ther. 1998, 77, 29.
48. (b) Blauer, G.; Akkawi, M.; Fleischhacker, W.; Hiessboeck, R. Chirality 1998, 10, 556.
49. (c) Egan, T. J.; Hunter, R.; Kaschula, C. H.; Marques, H. M.; Misplon, A.; Walden, J. J. Med. Chem. 2000, 43, 283.
50. Replacement of TBAF by CsF resulted in lower yields.