Oxidative Cross-Coupling of N-(2′-Phenylphenyl)benzene-sulfonamides or Benzoic and Naphthoic Acids with Alkenes Using a Palladium-Copper Catalyst System under Air

Journal of Organic Chemistry

Volumn 63, Issue 15, 1998, Pages 5211-5215

  Miura, Masahiro ^a   Tsuda, Takatoshi ^a   Satoh, Tetsuya ^a   Pivsa Art, Sommai ^a   Nomura, Masakatsu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000037010     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980584b     Document Type: Article

References (38)

1. For reviews, see: (a) Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. (b) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
2. For reviews, see: (a) Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451. (b) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
3. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
4. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
5. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
6. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
7. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
8. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
9. Carbonyl-directed catalytic reactions: (a) Murai, S.; Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N. Nature (London) 1993, 366, 529. (b) Murai, S. J. Synth. Org. Chem. Jpn. 1994, 54, 992. (c) Kakiuchi, F.; Sekine, S.; Tanaka, Y.; Kamatani, A.; Sonoda, M.; Chatani, N.; Murai, S. Bull. Chem. Soc. Jpn. 1995, 68, 62. (d) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett 1995, 679. (e) Kakiuchi, F.; Yamamoto, Y.; Chatani, N.; Murai, S. Chem. Lett. 1995, 681. (f) Sonoda, M.; Kakiuchi, F.; Kamatani A.; Chatani, N.; Murai, S. Chem. Lett. 1996, 109. (g) Trost, B. M.; Imi, K. Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371.
10. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
11. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
12. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
13. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
14. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
15. Nitrogen-directed catalytic reactions: (a) Moore, E. J.; Pretzer, W. R.; O'Connell, T. J.; Harris, J.; LaBounty, L.; Chou, L.; Grimmer, S. S. J. Am Chem. Soc. 1992, 114, 5888. (b) Aulwurm, U. R.; Melchinger, J. U.; Kisch, H. Organometallics 1995, 14, 3385. (c) Lim, Y.-G.; Kang, J.-B., Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1996, 2201. (d) Kakiuchi, F.; Yamauchi, M.; Chatani, N.; Murai, S. Chem. Lett. 1996, 111. (e) Chatani, N.; Fukuyama, T.; Kakiuchi, F.; Murai, S. J. Am. Chem. Soc. 1996, 118, 493. (f) Chatani, N.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1997, 62, 2604.
16. (a) Itoh, K.; Miura, M.; Nomura, M. Tetrahedron Lett. 1992, 33, 5369.
17. (b) Satoh, T.; Kokubo, K.; Miura, M.; Nomura, M. Organometallics 1994, 13, 4431.
18. (c) Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Mol. Catal. A: Chem. 1996, 111, 25.
19. (d) Satoh, T.; Tsuda, T.; Kushino, Y.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6476.
20. (e) Satoh, T.; Itaya, T.; Miura, M.; Nomura, M. Chem. Lett. 1996, 823.
21. (f) Satoh, T.; Ikeda, M.; Kushino, Y.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 2662.
22. (g) Satoh, T.; Ikeda, M.; Miura, M.; Nomura, M. J. Org. Chem. 1997, 62, 4877.
23. (h) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew Chem., Int. Ed. Engl. 1997, 36, 1740.
24. (i) Miura, M.; Tsuda, T.; Satoh, T.; Nomura, M. Chem. Lett. 1997, 1103.
25. (a) Canty, A. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 9, Chapter 5, p 225.
26. (b) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995; pp 87-94.
27. Preliminary attempts of coupling of the sulfonamides or acids with aryl iodides have not yet succeeded.
28. Palladium-catalyzed reaction of aromatic compounds with alkenes, which does not involve orthopalladation: Fujiwara, Y.; Jintoku, T.; Takaki, K. CHEMTECH 1990, 636. Reference 5b, pp 55-59.
29. Predrying of the base was found to be important (see the Experimental Section); without this process and/or in the absence of MS 4A, the yield of 3a was reduced to 77-84%. In the reaction of acid 13 with 2b without using MS 4A, the product yield was less than 10%. Thus, MS 4A as desiccant was always used.
30. In this case, air itself may directly act as an oxidant: Satoh, T.; Miura, M.; Nomura, M. J. Mol. Catal. A: Chem. 1996, 112, 211.
31. There would be also a possibility that a Pd-Cu complex participates in the reaction: Hosokawa, T.; Murahashi, S.-I. Acc. Chem. Res. 1990, 23, 49.
32. Dijkstra, G.; Kruizinga, W. H.; Kellogg, R. M. J. Org. Chem. 1987, 52, 4230.
33. See, for example: Albert, J.; Granell, J.; Luque, A.; Minguez, J.; Moragas, R.; Font-Bardía, M.; Solans, X. J. Organomet. Chem. 1996, 522, 87.
34. Wolfe, J. P.; Rennels, R. A.; Buchwald, S. L. Tetrahedron 1996, 52, 7525 and references therein.
35. Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
36. Bell, F. J. Chem. Soc. 1928, 2770.
37. Elix, J. A.; Murphy, D. P. Aust. J. Chem. 1975, 28, 1559.
38. Jones, P. R.; Weisman, G. R.; Baillargeon, M. J.; Gosink, T. A. J. Org. Chem. 1980, 45, 3618.