Pd(PhCN)2Cl2/P(t-Bu)3: A versatile catalyst for Sonogashira reactions of aryl bromides at room temperature

Organic Letters

Volumn 2, Issue 12, 2000, Pages 1729-1731

  Hundertmark, Thomas ^a   Littke, Adam F ^a   Buchwald, Stephen L ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BROMOBENZENE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS; TEMPERATURE;

ALKYNES; BROMOBENZENES; CATALYSIS; ORGANOMETALLIC COMPOUNDS; PALLADIUM; TEMPERATURE;

EID: 0034658926     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0058947     Document Type: Article

References (38)

1. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 4467-4470.
2. (b) Cassar, L. J. Organomet. Chem. 1975, 93, 253-257.
3. Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259-263.
4. (a) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: New York, 1998; Chapter 5.
5. (b) Brandsma, L.; Vasilevsky, S. F.; Verkruijsse, H. D. Application of Transition Metal Catalysts in Organic Synthesis; Springer-Verlag: Berlin, 1998; Chapter 10.
6. Rossi, R.; Carpita, A.; Bellina, F. Org. Prep. Proced. Int. 1995, 27, 127-160.
7. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 3, Chapter 2.4.
8. Nguefack, J.-F.; Bolitt, V.; Sinou, D. Tetrahedron Lett. 1996, 31, 5527-5530.
9. Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255-1261.
10. For pioneering studies, see the following references. (a) Carbonylation: Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386-1388. Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742-8744.
11. For pioneering studies, see the following references. (a) Carbonylation: Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1989, 28, 1386-1388. Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742-8744.
12. (b) Dechlorination: Ben-David, Y.; Gozin, M.; Portnoy, M.; Milstein, D. J. Mol. Catal. 1992, 73, 173-180.
13. (a) Coupling of vinyl-or arylsilanes: Gouda, K.-i.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233.
14. (b) Amine arylation: Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
15. (b) Amine arylation: Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
16. (b) Amine arylation: Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
17. (b) Amine arylation: Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370. Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
18. Suzuki reaction: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
19. Suzuki reaction: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
20. Suzuki reaction: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Bei, X.; Crevier, T.; Guram, A. S.; Jandeleit, B.; Powers, T. S.; Turner, H. W.; Uno, T.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 3855-3858.
21. Heck reaction: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132.
22. (e) Ketone arylation: Kawatsura, M.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 1473-1478.
23. (f) Alkoxide arylation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225. Watanabe, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1999, 40, 8837-8840.
24. (f) Alkoxide arylation: Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225. Watanabe, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1999, 40, 8837-8840.
25. (g) Amidocarbonylation: Kim, J. S.; Sen, A. J. Mol. Catal. A 1999, 143, 197-201.
26. (a) Suzuki reaction and amine arylation: Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
27. (b) Alkoxide arylation: Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
28. Ketone arylation: Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360-1370.
29. (a) Suzuki reaction: Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 1998, 37, 3387-3388.
30. (b) Heck reaction: Littke, A. F.; Fu, G. C. J. Org. Chem. 1999, 64, 10-11.
31. Stille reaction: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 1999, 38, 2411-2413.
32. 3 in palladium-catalyzed coupling reactions, see: Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620.
33. 3, essentially no reaction is observed even after 24 h at room temperature (≤ 5% yield).
34. (b) Preliminary experiments with recently reported biaryl dialkyl phosphines indicate that catalysts derived from these ligands, while useful at ∼50°C, are inefficient at room temperature. The origins of these differences in reactivity are being investigated in our laboratories.
35. 3 provides a slightly less active catalyst.
36. (b) Toluene and THF may be used in place of dioxane.
37. Couplings proceed extremely slowly in the absence of CuI.
38. 2]Br is observed. After the aryl bromide has been consumed, the reaction mixture is diluted with EtOAc (5 mL), filtered through a small pad of silica gel (with EtOAc rinsings), concentrated, and purified by flash chromatography.