Heck reactions in the presence of P(t-Bu)3: Expanded scope and milder reaction conditions for the coupling of aryl chlorides

Journal of Organic Chemistry

Volumn 64, Issue 1, 1999, Pages 10-11

  Littke, Adam F ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORIDE; PHOSPHINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033534423     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9820059     Document Type: Article

References (37)

1. The low reactivity of aryl chlorides in cross-coupling reactions is generally ascribed to their reluctance to oxidatively add to Pd(0). For a discussion, see: Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
2. For reviews of the Heck reaction, see: (a) Bräse, S.; de Meijere, A. In Metal Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley: New York, 1998; Chapter 3.
3. (b) Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
4. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379-2411.
5. (d) Heck, R. F. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 4, Chapter 4.3.
6. (a) Chlorobenzene and electron-poor aryl chlorides (150 °C): Ben-David, Y.; Portnoy, M.; Gozin, M.; Milstein, D. Organometallics 1992, 11, 1995-1996.
7. (b) Chloroanisole, chlorobenzene, and electron-poor aryl chlorides (140 °C): Portnoy, M.; Ben-David, Y.; Milstein, D. Organometallics 1993, 12, 4734-4735.
8. (c) Portnoy, M.; Ben-David, Y.; Rousso, I.; Milstein, D. Organometallics 1994, 13, 3465-3479.
9. (a) 4-Chlorobenzaldehyde (150 °C): Herrmann, W. A.; Brossmer, C.; Ofele, K.; Beller, M.; Fischer, H. J. Mol. Catal. A 1995, 103, 133-146.
10. (b) Electron-poor aryl chlorides (130 °C): Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844-1848. Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Reirmeier, T. H.; Ofele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357-1364.
11. (b) Electron-poor aryl chlorides (130 °C): Herrmann, W. A.; Brossmer, C.; Ofele, K.; Reisinger, C.-P.; Priermeier, T.; Beller, M.; Fischer, H. Angew. Chem., Int. Ed. Engl. 1995, 34, 1844-1848. Herrmann, W. A.; Brossmer, C.; Reisinger, C.-P.; Reirmeier, T. H.; Ofele, K.; Beller, M. Chem. Eur. J. 1997, 3, 1357-1364.
12. (c) Electron-poor aryl chlorides (130 °C): Herrmann, W. A.; Elison, M.; Fischer, J.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 2371-2374.
13. Chlorotoluene, chlorobenzene, and chlorobenzaldehyde (150 °C): Reetz, M. T.; Lohmer, G.; Schwickardi, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 481-483.
14. Electron-poor aryl chlorides (140-160 °C): Beller, M.; Zapf, A. Synlett 1998, 792-793.
15. For an overview of Heck couplings of aryl chlorides, see: Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301-309.
16. Electron-poor aryl halides oxidatively add to Pd(0) more readily than do the corresponding electron-rich aryl halides. For a discussion, see refs 1 and 2.
17. Suzuki cross-coupling: Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed., in press.
18. For example, see: (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.
19. For example, see: (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.
20. (b) Dechlorination: Ben-David, Y.; Gozin, M.; Portnoy, M.; Milstein, D. J. Mol. Catal. 1992, 73, 173-180.
21. (c) Cross-coupling with vinylsilanes and arylsilanes: Gouda, K.-i.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233.
22. (d) Suzuki cross-coupling: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Old, D. W., Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
23. (d) Suzuki cross-coupling: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Old, D. W., Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
24. (d) Suzuki cross-coupling: Shen, W. Tetrahedron Lett. 1997, 38, 5575-5578. Firooznia, F.; Gude, C.; Chan, K.; Satoh, Y. Tetrahedron Lett. 1998, 39, 3985-3988. Old, D. W., Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
25. (e) Amination: 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. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
26. (e) Amination: 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. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
27. (e) Amination: 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. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
28. (e) Amination: 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. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
29. For example, see: (a) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655-1664. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665-1673. Reference 3.
30. For example, see: (a) Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1655-1664. Portnoy, M.; Milstein, D. Organometallics 1993, 12, 1665-1673. Reference 3.
31. (b) Reference 4a.
32. (c) Beller has shown that Heck reactions of electron-poor aryl chlorides can be effected with electron-poor phosphites as ligands: Reference 6.
33. a data for phosphines, see: Rahman, M. M.; Liu, H.-Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1989, 8, 1-7.
34. a data for phosphines, see: Rahman, M. M.; Liu, H.-Y.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1989, 8, 1-7.
35. 2O, filtered through a pad of Celite, concentrated, and purified by flash chromatography (5% EtOAc/hexane), which yielded 118 mg (79%) of methyl cinnamate.
36. 2 leads to a slower reaction.
37. 3 display comparable effectiveness as bases.