Synthesis of diaryl ethers, diaryl thioethers, and diarylamines mediated by potassium fluoride-alumina and 18-crown-6: Expansion of scope and utility

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6338-6343

  Sawyer, J Scott ^a   Schmittling, Elisabeth A ^a   Palkowitz, Jayne A ^a   Smith III, William J ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ETHER DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFIDE;

ARTICLE; CYCLIZATION; ELECTRON TRANSPORT; REACTION ANALYSIS; SYNTHESIS;

EID: 0032483549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980800g     Document Type: Article

References (76)

1. Portions of this work have been presented at the following conferences: (a) Schmittling, E. A.; Sawyer, J. S. Presented at the 205th National Meeting of the American Chemical Society, Denver, CO, March 28-April 2, 1993. (b) Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 64. (c) Smith, W. J., III.; Schmittling, E. A.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 65.
2. Portions of this work have been presented at the following conferences: (a) Schmittling, E. A.; Sawyer, J. S. Presented at the 205th National Meeting of the American Chemical Society, Denver, CO, March 28-April 2, 1993. (b) Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 64. (c) Smith, W. J., III.; Schmittling, E. A.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 65.
3. Portions of this work have been presented at the following conferences: (a) Schmittling, E. A.; Sawyer, J. S. Presented at the 205th National Meeting of the American Chemical Society, Denver, CO, March 28-April 2, 1993. (b) Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 64. (c) Smith, W. J., III.; Schmittling, E. A.; Sawyer, J. S. Abstracts of Papers, 208th National Meeting of the American Chemical Society, Washington, DC, August 21-26, 1994; American Chemical Society: Washington, DC, 1994; ORGN 65.
4. (a) Deshpande, V. E.; Gohkhale, N. J. Tetrahedron Lett. 1992, 33, 4213-4216.
5. (b) Boger, D. L.; Sakaya, S. M.; Yohannes, D. J. Org. Chem. 1991, 56, 4204-4207.
6. Gottsegen, A.; Vermes, B.; Kajtarperedy, M.; Bihatsikarasai, E.; Nogradi, M. Tetrahedron Lett. 1988, 29, 5039-5040.
7. Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913.
8. Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498-2502.
9. (a) Sawyer, J. S. Drugs Future 1996, 21, 610-614.
10. (b) Sawyer, J. S. Expert Opin. Invest. Drugs 1996, 5, 73-77.
11. Johnson, W. O.; Kollman, G. E.; Swithenbank, C.; Yih, R. Y. J. Agric. Food Chem. 1978, 26, 285-287.
12. (a) Couladouros, E. A.; Soufli, I. C. Tetrahedron Lett. 1995, 36, 9369-9372.
13. (b) Rao, A. V. R.; Chakraborty, T. K.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1992, 33, 4799-4802.
14. (c) Boger, D. L.; Yohannes, D. J. Org. Chem. 1991, 56, 1763-1767.
15. (d) Boger, D. L.; Yohannes, D. J. Org. Chem. 1990, 55, 6000-6017.
16. (e) Jung, M. E.; Jachiet, D.; Rohloff, J. C. Tetrahedron Lett. 1989, 30, 4211-4214.
17. (f) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
18. (g) Boger, D. L.; Yohannes, D. J. Org. Chem. 1988, 53, 487-499.
19. Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364.
20. (a) Zhu, J. Synlett 1997, 133-144 and references therein.
21. (b) Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721-4736.
22. (c) Boger, D. L.; Zhou, J. C.; Borzilleri, R. M.; Nukui, S.; Castle, S. L. J. Org. Chem. 1997, 62, 4721-4736.
23. (d) Beugelmans, R.; Zamora, E. G.; Roussi, G. Tetrahedron Lett. 1997, 38, 8189-8192.
24. (e) Rao, A. V. R.; Gurjar, M. K.; Lakshmipathi, P., Reddy, M. M.; Nagarajan, M.; Pal, S.; Sarma, B. V. N. B. S.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 7433-7436.
25. (f) BoisChoussy, M.; Vergne, C.; Neuville, L.; Beugelmans, R.; Zhu, J. Tetrahedron Lett. 1997, 38, 5795-5798.
26. (g) Roussi, G.; Zamora, E. G.; Carbonnelle, A.-C., Beugelmans, R. Tetrahedron Lett. 1997, 38, 4401-4404.
27. (h) Roussi, G.; Zamora, E. G.; Carbonnelle, A.-C., Beugelmans, R. Tetrahedron Lett. 1997, 38, 4405-4406.
28. (i) Vergne, C.; BoisChoussy, M.; Beugelmans, R., Zhu, J. Tetrahedron Lett. 1997, 38, 1403-1406.
29. (j) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488-6495.
30. (k) Boger, D. L.; Zhou, J. J. Org. Chem. 1996, 61, 3938-3939.
31. (a) Pearson, A. J.; Zhang, P. L.; Bignan, G. J. Org. Chem. 1997, 62, 4536-4538.
32. (b) Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581-6586.
33. (c) Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940-3941.
34. (d) Pearson, A. J.; Bignan, G. Tetrahedron Lett. 1996, 37, 735-738.
35. (e) Pearson, A. J.; Park, J. G.; Zhu, P. Y. J. Org. Chem. 1992, 57, 3583-3589.
36. (f) Pearson, A. J.; Bruhn, P. R. J. Org. Chem. 1991, 56, 7092-7097.
37. (a) Konishi, H.; Okuno, T.; Nishiyama, S.; Yamamura, S.; Koyasu, K.; Terada, Y. Tetrahedron Lett. 1996, 37, 8791-8794.
38. (b) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937.
39. (c) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6043-6046.
40. (d) Evans, D. A. Ellman, J. A.; DeVries, K. M. J. Am. Chem. Soc. 1989, 111, 8912-8914.
41. (a) Jung, M. E.; Starkey, L. S. Tetrahedron 1997, 53, 8815-8824.
42. (b) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366.
43. (a) Olsen, R. K.; Feng, X.; Campbell, M.; Shao, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
44. (b) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812.
45. (a) Protiva, M. Drugs Future 1991, 16, 911-916.
46. (b) Hobbs, D. W.; Still, D. W. Tetrahderon Lett. 1987, 28, 2805-2808.
47. (a) Gorvin, J. H. J. Chem. Soc., Perkin Trans. 1 1988, 1331-1335.
48. (b) Kulagowski, J. J.; Rees, C. W. Synthesis 1980, 215.
49. Schmittling, E. A.; Sawyer, J. S. J. Org. Chem. 1993, 58, 3229-3230.
50. For pioneer reports detailing the condensation of phenols with highly activated aryl chlorides mediated by potassium fluoride- alumina, see: (a) Kang, R. H.; Zhu, J. S.; Li, W. Z.; Liu, S. R. Chin. Chem. Lett. 1990, 1, 55-56.
51. (b) Hwang, K.-J.; Park, S. K. Synth. Commun. 1990, 20, 949-954.
52. (a) Schmittling, E. A.; Sawyer, J. S. Tetrahedron Lett. 1991, 7207-7210.
53. (b) For a review of organic reactions on alumina, see: Kabalka, G. W.; Pagni, R. M. Tetrahedron 1997, 53, 7999-8065.
54. Under the standard acetonitrile conditions, no reaction was also observed when 3-methoxyphenol was reacted with either 2- or 4-chlorobenzonitrile, even after prolonged periods (9 days) and in the presence of large quantities of potassium fluoride-alumina (2.5 wt equiv based on 3-methoxyphenol).
55. Jackson, W. T.; Froelich, L. L.; Gapinski, D. M.; Mallett, B. E.; Sawyer, J. S. J. Med. Chem. 1993, 36, 1726-1734.
56. The exact nature of the active basic species present in potassium fluoride-alumina reagents has been the subject of some controversy, see: (a) Ando, T.; Clark, J. H.; Cork, D. G.; Hanafusa, T.; Ichihara, J.; Kimura, T. Tetrahedron Lett. 1987, 28, 1421-1424.
57. (b) Weinstock, L. M.; Stevenson, J. M.; Tomellini, S. A.; Pan, S.-H.; Utne, T.; Jobson, R. B.; Reinhold: D. F. Tetrahedron Lett 1986, 27, 3845-3848.
58. Sawyer, J. S.; Bach, N. J.; Baker, S. R.; Baldwin, R. F.; Borromeo, P. S.; Cockerham, S. L.; Fleisch, J. H.; Floreancig, P.; Froelich, L. L.; Jackson, W. T.; Marder, P.; Palkowitz, J. A.; Roman, C. R.; Saussy, D. L., Jr.; Schmittling, E. A.; Silbaugh, S. A.; Spaethe, S. M.; Stengel, P. W.; Sofia, M. J. J. Med. Chem. 1995, 38, 4411-4432.
59. Ghosal, S.; Banerjee, S.; Chauhan, R. B. P. S.; Srivastava, R. S. J. Chem. Soc., Perkin Trans. 1 1977, 740-743.
60. (a) Kajimoto, T.; Yahiro, K.; Nohara, T. Chem. Lett. 1988, 1113-1114.
61. (b) Fuchigami, T.; Awata, T.; Nonaka, T.; Baizer, M. M. Bull. Soc. Chem. Jpn. 1986, 59, 2873-2879.
62. (c) Brunelle, D. J.; Singleton, D. A. Tetrahedron Lett. 1984, 25, 3383-3386.
63. (d) Wright, J.; Jorgensen, E. C. J. Org. Chem. 1968, 33, 1245-1246.
64. For a discussion of the radical nature of the addition of phenolate to p-dinitrobenzene, see: Mir, M.; Espin, M.; Marquet, J.; Gallardo, I.; Tomasi, C. Tetrahedron Lett. 1994, 35, 9055-9058.
65. (a) Shevelev, S. A.; Dutov, M. D.; Vatsadze, I. A.; Seruchkina, O. V.; Korolev, M. A.; Rusanov, A. L. Russ. Chem. Bull. 1995, 44, 384-385.
66. (b) Sammes, P. G.; Thetford, D.; Voyle, M. J. Chem. Soc., Perkin Trans. 1 1988, 3229-3231.
67. (c) Clark, J. H.; Owen, N. D. S. Tetrahedron Lett. 1987, 28, 3627-3630.
68. (d) Gorvin, J. H. J. Chem. Soc., Chem. Commun. 1985, 238-239.
69. (e) Williams, F. J.; Donahue, P. E. J. Org. Chem. 1977, 42, 3414-3419.
70. Clark, J. H.; Smith, D. K. Tetrahedron Lett. 1985, 26, 2233-2236.
71. Cella, J. A.; Bacon, S. W. J. Org. Chem. 1984, 49, 1122-1125.
72. Maggini, M.; Passudetti, M.; Gonzales-Trueba, G.; Prato, M.; Quintily, U.; Scorrano, G. J. Org. Chem. 1991, 56, 6406-6411.
73. Archer, S.; Pica-Mattoccia, L.; Cioli, D.; Seyed-Mozaffari, A.; Zayed, A.-H. J. Med. Chem. 1988, 31, 254-260.
74. Beaumont, A. J.; Clark, J. H.; Boechat, N. A. J. Fluorine Chem. 1993, 63, 25-30.
75. Yeager, G. W.; Schissel, D. N. Synthesis 1991, 63-68.
76. Smith, W. J., III.; Sawyer, J. S. Tetrahedron Lett. 1996, 37, 299-302.