Novel electron-rich bulky phosphine ligands facilitate the palladium- catalyzed preparation of diaryl ethers

Journal of the American Chemical Society

Volumn 121, Issue 18, 1999, Pages 4369-4378

  Aranyos, Attila ^a   Old, David W ^a   Kiyomori, Ayumu ^a   Wolfe, John P ^a   Sadighi, Joseph P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIARYL ETHER; ETHER DERIVATIVE; HALOGENATED HYDROCARBON; LIGAND; PALLADIUM; PHENOL DERIVATIVE; PHOSPHINE DERIVATIVE; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; ELECTRON TRANSPORT; ORGANIC CHEMISTRY; REDUCTION; SYNTHESIS; TEMPERATURE;

EID: 0033549049     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990324r     Document Type: Article

References (78)

1. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
2. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
3. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
4. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
5. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
6. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
7. For examples of medicinally important diaryl ethers, see : (a) Evans, D. A., DeVries, K. M. In Glycopeptide Antibiotics, Drugs and the Pharmaceutical Sciences; Nagarajan, R., Ed.; Marcel Decker, Inc.: New York, 1994; Vol. 63, pp 63-104. (b) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216. (c) Singh, S. B.; Pettit, G. R. J. Org. Chem. 1990, 55, 2797-2800. (d) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540. (e) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913. (f) Atkinson, D. C.; Godfrey, K. E.; Myers, P. L.; Philips, N. C.; Stillings, M. R.; Welbourn, A. P. J. Med. Chem. 1983, 26, 1361-1364; For examples of agriculturally important diaryl ethers, see: (g) Seldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1998; pp 62-65.
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12. For examples of recent work in diaryl ether formation, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 2937-2940. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (c) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (d) Palomo, C.; Oairbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 19, 2091-2092. (e) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. Chem. Commun. 1994, 439-440.
13. For examples of recent work in diaryl ether formation, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 2937-2940. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (c) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (d) Palomo, C.; Oairbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 19, 2091-2092. (e) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. Chem. Commun. 1994, 439-440.
14. For examples of recent work in diaryl ether formation, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 2937-2940. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (c) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (d) Palomo, C.; Oairbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 19, 2091-2092. (e) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. Chem. Commun. 1994, 439-440.
15. For examples of recent work in diaryl ether formation, see: (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 2937-2940. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J. J. Org. Chem. 1998, 63, 6338-6343. (c) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495. (d) Palomo, C.; Oairbide, M.; López, R.; Gómez-Bengoa, E. Chem. Commun. 1998, 19, 2091-2092. (e) Beugelmans, R.; Zhu, J.; Husson, N.; Bois-Choussy, M.; Singh, G. P. Chem. Commun. 1994, 439-440.
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19. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Hartwig, J. F. Synlett 1997, 329-340. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem., in press.
20. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Hartwig, J. F. Synlett 1997, 329-340. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem., in press.
21. For reviews, see: (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067. (c) Hartwig, J. F. Synlett 1997, 329-340. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem., in press.
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27. (b) Doye, S.; Buchwald, S. L., unpublished Results.
28. For other examples of bulky, electron-rich ligands for Pd-catalyzed carbon-heteroatom bond forming reactions, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367- 2370. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1998, 39, 617-620. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369- 7370. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
29. For other examples of bulky, electron-rich ligands for Pd-catalyzed carbon-heteroatom bond forming reactions, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1998, 39, 617-620. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369- 7370. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
30. For other examples of bulky, electron-rich ligands for Pd-catalyzed carbon-heteroatom bond forming reactions, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367- 2370. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1998, 39, 617-620. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369- 7370. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
31. For other examples of bulky, electron-rich ligands for Pd-catalyzed carbon-heteroatom bond forming reactions, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367- 2370. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1998, 39, 617-620. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
32. For other examples of bulky, electron-rich ligands for Pd-catalyzed carbon-heteroatom bond forming reactions, see: (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620. (b) Yamamoto, M.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367- 2370. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1998, 39, 617-620. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369- 7370. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
33. Typically, oxidative addition of aryl chlorides to Pd(0) requires temperatures of 60-140°C. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062. (b) Hermann, W. A.; Brossmer, C.; Priermeier, T.; Öfele, K. J. Organomet. Chem. 1994, 481, 97-108. (c) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366. (d) Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. 1989, 28, 1386-1388.
34. Typically, oxidative addition of aryl chlorides to Pd(0) requires temperatures of 60-140°C. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062. (b) Hermann, W. A.; Brossmer, C.; Priermeier, T.; Öfele, K. J. Organomet. Chem. 1994, 481, 97-108. (c) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366. (d) Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. 1989, 28, 1386-1388.
35. Typically, oxidative addition of aryl chlorides to Pd(0) requires temperatures of 60-140°C. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062. (b) Hermann, W. A.; Brossmer, C.; Priermeier, T.; Öfele, K. J. Organomet. Chem. 1994, 481, 97-108. (c) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366. (d) Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. 1989, 28, 1386-1388.
36. Typically, oxidative addition of aryl chlorides to Pd(0) requires temperatures of 60-140°C. (a) Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062. (b) Hermann, W. A.; Brossmer, C.; Priermeier, T.; Öfele, K. J. Organomet. Chem. 1994, 481, 97-108. (c) Parshall, G. W. J. Am. Chem. Soc. 1974, 96, 2360-2366. (d) Huser, M.; Youinou, M.-T.; Osborn, J. A. Angew. Chem., Int. Ed. 1989, 28, 1386-1388.
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49. 8e we employed dicylclohexylphenylphosphine in a control reaction due the commercial availability of this compound.
50. Control experiments were carried out in the absence of a palladium salt. For the reaction of 4-bromoacetophenone and phenol with potassium phosphate in toluene at 100°C, none of the desired product was detected; in DMF at 100°C, 32% (GC, corrected) of the starting halide was consumed, and a 5% GC yield of the desired product was observed.
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