Facile N-arylation of amines and sulfonamides and O-arylation of phenols and arenecarboxylic acids

Journal of Organic Chemistry

Volumn 71, Issue 8, 2006, Pages 3198-3209

  Liu, Zhijian ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARENECARBOXYLIC ACIDS; N-ARYLATION; O-SILYLARYL INFLATES;

CARBOXYLIC ACIDS; PHENOLS; REACTION KINETICS; SULFONATION; TRANSITION METALS;

AMINES;

ALIPHATIC AMINE; AMINE; AROMATIC CARBOXYLIC ACID; BENZOIC ACID PHENYL ESTER; CARBAMIC ACID DERIVATIVE; CESIUM; CESIUM FLUORIDE; DIPHENYL ETHER; DIPHENYLAMINE; FUNCTIONAL GROUP; N PROPARGYLANILINE; N,N DIPHENYLBENZENESULFONAMIDE; PHENOL DERIVATIVE; SILANE DERIVATIVE; SULFONAMIDE; TRANSITION ELEMENT; TRIFLUOROMETHANESULFONIC ACID; TRIPHENYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ALKYLATION; AMINES; CARBAMATES; CARBOXYLIC ACIDS; FURANS; MOLECULAR STRUCTURE; PHENOLS; SULFONAMIDES;

EID: 33645768327     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0602221     Document Type: Article

References (73)

1. (a) Negwer, M. In Organic-Chemical Drugs and their Synonyms (An International Survey), 7th ed.; Akademie Verlag GmbH: Berlin, Germany, 1994.
2. (b) Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112-113.
3. (c) Hong, Y.; Senanayake, C. H.; Xiang, T.; Vandenbossche, C. P.; Tanoury, G. J.; Bakale, R. P.; Wald, S. A. Tetrahedron Lett. 1998, 39, 3121-3124.
4. (d) Romero, D. L.; Morge, R. A.; Genin, M. J.; Biles, C.; Busso, M.; Resnick, L.; Althaus, I. W.; Reusser, F.; Thomas, R. C.; Tarpley, W. G. J. Med. Chem. 1993, 36, 1505-1508.
5. (e) 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.
6. (f) Pettit, G. R.; Singh, S. B.; Niven, M. L. J. Am. Chem. Soc. 1988, 110, 8539-8540.
7. (g) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909-4913.
8. (h) 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.
9. (i) Nicolaou, K. C.; Christopher, N. C. B. J. Am. Chem. Soc. 2002, 124, 10451-10455.
10. CRC Handbook of Pesticides; Milne, G. W. A., Ed.; CRC Press: Boca Raton, FL, 1994.
11. Turner, S. R.; Strohbach, J. W.; Tommasi, R. A.; Aristoff, P. A.; Johnson, P. D.; Skulnick, H. I.; Dolak, L. A.; Seest, E. P.; Tomich, P. K.; Bohanon, M. J.; Horng, M. M.; Lynn, J. C.; Chong, K.-T.; Hinshaw, R. R.; Watenpaugh, K. D.; Janakiraman, M. N.; Thaisrivongs, S. J. Med. Chem. 1998, 41, 3467-3476.
12. (a) Goodson, F. E.; Hartwig, J. F. Macromolecules 1998, 31, 1700-1703.
13. (b) Goodson, F. E.; Hauck, S. I.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 7527-7530.
14. (c) Singer, R. A.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 213-214.
15. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382-2384.
16. (b) Goodbrand, H. B.; Hu, N.-X. J. Org. Chem. 1999, 64, 670-674.
17. (c) Ullmann, F. Chem. Ber. 1904, 37, 853-854.
18. (a) Lindley, J. Tetrahedron 1984, 40, 1433-1456.
19. (b) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1370.
20. (a) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793-796.
21. (b) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 581-584.
22. (c) He, H.; Wu, Y.-J. Tetrahedron Lett. 2003, 44, 3385-3386.
23. For a recent review, see: (d) Sawyer, J. S. Tetrahedron 2000, 56, 5045-5065.
24. (e) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345-2347.
25. (a) Wolfe, J. P.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
26. (b) Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413-2415.
27. (c) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885-2888.
28. (d) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
29. (e) Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369-4378.
30. (f) Marcoux, J.; Doye, S.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 10539-10540.
31. (g) Kuwabe, S.-I.; Torraca, K. E.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 12202-12206.
32. (a) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 853-860.
33. (b) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
34. (c) Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224-3225.
35. (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940.
36. (b) Decicco, C. P.; Song, S.; Evans, D. A. Org. Lett. 2001, 3, 1029-1032.
37. Chan, D. M. T.; Monaco, K. L.; Wang, R.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
38. (a) Combs, A. P.; Rafalski, M. J. Comb. Chem. 2000, 2, 29-32.
39. (b) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
40. Deng, B.-L.; Lepoivre, J. A.; Lemiere, G. Eur. J. Org. Chem. 1999, 2683-2689.
41. Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287-289.
42. (a) Yamamoto, T. Synth. Commun. 1979, 9, 219-222.
43. (b) Ramesh, C.; Kubota, Y.; Miwa, M.; Sugi, Y. Synthesis 2002, 2171-2173.
44. Beyer, H.; Walter, W. Handbook of Organic Chemistry; Prentice Hall Europe: London, UK, 1996; p 497.
45. (a) Fischer, E. Ber. 1895, 28, 3254-3257.
46. (b) Butts, J. J. Am. Chem. Soc. 1931, 53, 3560-3561.
47. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211-1214.
48. (a) Yoshida, H.; Shirakawa, E.; Honda, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2002, 41, 3247-3249.
49. (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed. 2004, 43, 3935-3938.
50. (c) Yoshida, H.; Sugiura, S.; Kunai, A. Org. Lett. 2002, 4, 2767-2769.
51. (a) Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659-2661.
52. (b) Yoshida, H.; Watanabe, M.; Fukushima, H.; Ohshita, J.; Kunai, A. Org. Lett. 2004, 6, 4049-4051.
53. Beller, M.; Breindl, C.; Riermeier, T. H.; Tillack, A. J. Org. Chem. 2001, 66, 1403-1412.
54. (a) Liu, Z.; Larock, R. C. Org. Lett. 2003, 5, 4673-4675.
55. (b) Liu, Z.; Larock, R. C. Org. Lett. 2004, 6, 99-102.
56. Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827-5828.
57. Yoshida, H.; Ikadai, J.; Shudo, M.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2003, 125, 6638-6639.
58. Silylaryl triflate 1e was prepared from 2-bromo-4,6-dimethylphenol in a manner similar to the preparation of silylaryl triflate 1c.
59. 4-Aminopyridine and 2-aminopyridine react with the silylaryl triflate 1a to afford an unknown salt; no N-arylated products were isolated under our usual reaction conditions.
60. Liu, Z.; Zhang, X.; Larock, R. C. J. Am. Chem. Soc. 2005, 127, 15716-15717.
61. Wittig, G.; Reichel, B. Ber. 1963, 96, 2851-2858.
62. No simple N-arylation product from indole is isolated, when indole is allowed to react with silylaryl triflate 1a under our usual reaction conditions.
63. Kessar, S. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, England, 1991; Vol. 4, pp 483-515.
64. (a) He, H.; Wu, Y. J. Tetrahedron Lett. 2003, 44, 3385-3386.
65. (b) Yin, J.; Buchwald, S. L. Org. Lett. 2002, 4, 1101-1104.
66. Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029-3036.
67. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553-5566.
68. Yoshida, Y.; Tanabe, Y. Synthesis 1997, 533-535.
69. Haga, K.; Oohashi, M.; Kaneko, R. Bull. Chem. Soc. Jpn. 1984, 57, 1586-1590.
70. Shi, L.; Wang, M.; Fan, Ch.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515-3517.
71. Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799-3802.
72. Glatzhofer, D. T.; Roy, R. R.; Cossy, K. N. Org. Lett. 2002, 4, 2349-2352.
73. Lee, C. K.; Yu, J. S.; Kim, S. H. J. Heterocycl. Chem. 1998, 35, 835-841.