Simple, efficient catalyst system for the palladium-catalyzed amination of aryl chlorides, bromides, and triflates

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1158-1174

  Wolfe, John P ^a,c   Tomori, Hiroshi ^c   Sadighi, Joseph P ^b,c   Yin, Jingjun ^c   Buchwald, Stephen L ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^c MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE DERIVATIVE; CHLORINE DERIVATIVE; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFONIC ACID DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

AMINES; ANILINE COMPOUNDS; BIPHENYL COMPOUNDS; BROMOBENZENES; CATALYSIS; CHLOROBENZENES; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PALLADIUM; TEMPERATURE;

EID: 0034712156     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991699y     Document Type: Article

References (86)

1. (a) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
2. (b) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046-2067.
3. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
4. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617-620.
5. (b) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367-2370.
6. (c) Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807-4810.
7. (d) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369-7370.
8. (e) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
9. (f) Bei, X.; Guram, A. S.; Turner, H. W.; Weinberg, W. H. Tetrahedron Lett. 1999, 40, 1237-1240.
10. (g) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Peterson, J. L. Organometallics 1999, 18, 1840-1853.
11. (h) A procedure employing the Herrmann-Beller palladacycle has been used for some C-N bond-forming reactions of aryl chlorides at 135 °C; mixtures of regioisomers are often observed. Riermeier, T. H.; Zapf, A.; Beller, M. Top. Catal. 1997, 4, 301-309 and references therein.
12. 3. See: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580. (e) Nolan has also recently reported animations of aryl chlorides using nucleophilic carbenes as ligand. See: Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
13. 3. See: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580. (e) Nolan has also recently reported animations of aryl chlorides using nucleophilic carbenes as ligand. See: Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
14. 3. See: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580. (e) Nolan has also recently reported animations of aryl chlorides using nucleophilic carbenes as ligand. See: Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
15. 3. See: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580. (e) Nolan has also recently reported animations of aryl chlorides using nucleophilic carbenes as ligand. See: Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
16. 3. See: Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580. (e) Nolan has also recently reported animations of aryl chlorides using nucleophilic carbenes as ligand. See: Huang, J.; Grasa, G.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
17. Ligands 3 and 4 are commercially available from Strem Chemical Co.
18. Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
19. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
20. (b) Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609-3612.
21. (c) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217-7218.
22. (d) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568-1569.
23. (e) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327-5330.
24. Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367-6370.
25. The Pd-catalyzed arylation of benzophenone hydrazone and the subsequent transformation of the aryl hydrazone products to indoles have been previously reported by this group. See: (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (c) Hartwig has also reported the catalyzed arylation step, but not the subsequent conversion into indoles: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2090-2093.
26. The Pd-catalyzed arylation of benzophenone hydrazone and the subsequent transformation of the aryl hydrazone products to indoles have been previously reported by this group. See: (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (c) Hartwig has also reported the catalyzed arylation step, but not the subsequent conversion into indoles: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2090-2093.
27. The Pd-catalyzed arylation of benzophenone hydrazone and the subsequent transformation of the aryl hydrazone products to indoles have been previously reported by this group. See: (a) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 6621-6622. (b) Wagaw, S.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10251-10263. (c) Hartwig has also reported the catalyzed arylation step, but not the subsequent conversion into indoles: Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2090-2093.
28. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240-7241.
29. Hartwig has also demonstrated the displacement of triarylphosphines by pyridine in LPd(Ar)X complexes. See: Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030-3039.
30. Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359-6362.
31. Use of ligand 3 for the reaction of 2-bromo-p-xylene with N-methylaniline gave only 60% conversion.
32. Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1987, 109, 5478-5486.
33. (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267.
34. (b) Åhman, J.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6363-6366.
35. (c) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268-1273.
36. Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 4960-4976.
37. Kranenburg, M.; van der Burgt, Y. E. M.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Goubitz, K.; Fraanje, J. Organometallics 1995, 14, 3081-3089.
38. Grushin, V. V.; Alper, H. Chem. Rev. 1994, 94, 1047-1062.
39. (a) Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633.
40. (b) Hartwig, J. F.; Paul, F. J. Am. Chem. Soc. 1995, 117, 5373-5374.
41. (c) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969-5970.
42. (d) Louie, J.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 11598-11599.
43. (e) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1995, 117, 4708-4709.
44. (f) Louie, J.; Paul, F.; Hartwig, J. F. Organometallics 1996, 15, 2794-2805.
45. (g) Hartwig, J. F. Synlett 1997, 329-340.
46. (h) Jones has demonstrated that steric bulk facilitates C-C bond-forming reductive elimination in ruthenium complexes, see: Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615-2622.
47. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710- 712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714- 7715.
48. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710- 712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714- 7715.
49. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710- 712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714- 7715.
50. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710-712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714- 7715.
51. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710- 712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714- 7715.
52. Metal-π interactions have been observed in other palladium complexes. (a) Ossor, H.; Pfeffer, M.; Jastrzebski, J. T. B. H.; Stam, C. H. Inorg. Chem. 1987, 26, 1169-1171. (b) Falvello, L. R.; Fornies, J.; Navarro, R.; Sicilia, V.; Tomas, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 891-893. (c) Sommovigo, M.; Pasquali, M.; Leoni, P.; Braga, D.; Sabatino, P. Chem. Ber. 1991, 124, 97-99. Li, C.-S.; Cheng, C.-H.; Liao, F.-L.; Wang, S.-L. J. Chem. Soc., Chem. Commun. 1991, 710- 712. (e) Kannan, S.; James, A. J.; Sharp, P. R. J. Am. Chem. Soc. 1998, 120, 215-216. (f) Kočovský, P.; Vyskoc̄il, S.; Císařová, I.; Sejbal, J.; Tišlerová, I.; Smrčina, M.; Lloyd-Jones, G. C.; Stephen, S. C.; Butts, C. P.; Murray, M.; Langer, V. J. Am. Chem. Soc. 1999, 121, 7714-7715.
53. Biaryl-forming reductive elimination from Pt(II) has been postulated to occur via a transition state in which both arenes are perpendicular to the coordination plane. See: Braterman, P. S.; Cross, R. J.; Young, G. B. J. Chem. Soc., Dalton Trans. 1977, 1892-1897.
54. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
55. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133-1135.
56. Tsuji, Y.; Huh, K. T.; Ohsugi, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1365-1370.
57. Watanabe, Y.; Tsjui, Y.; Ige, H.; Ohsuji, Y.; Ohta, T. J. Org. Chem. 1984, 49, 3359-3363.
58. Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054-6058.
59. Walkup, R. E.; Searles, S., Jr. Tetrahedron 1985, 41, 101-106.
60. Kotsuki, H.; Kobayashi, S.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1145-1147.
61. Pratt, E. F.; McGovern, T. P. J. Org. Chem. 1964, 29, 1540-1543.
62. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 6066-6068.
63. Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. T. J. Chem. Soc., Perkin Trans. 1 1991, 2095-2102.
64. Vernaudon, P.; Rajoharison, H. G.; Roussel, C. Bull. Chem. Soc. Fr. 1987, 205-211.
65. Haga, K.; Oohashi, M.; Kaneko, R. B. Chem. Soc. Jpn. 1984, 57, 1586-1590.
66. Dictionary of Organic Compounds, 6th ed.; Cadogan, J. I. G., Ley, S. V., Pattenden, G., Raphael, R. A., Rees, C. W., Eds.; Chapman & Hill: London, 1996; p 2611.
67. Marsden, R. J. B. J. Chem. Soc. 1937, 627.
68. Davis, W.; Ross, W. C. J. J. Chem. Soc. 1949, 2831-2834.
69. Busch, M.; Kunder, H. Ber. Dtsch. Chem. Ges. 1916, 49, 317-334.
70. Shim, S. C.; Huh, K. T.; Park, W. H. Tetrahedron 1986, 42, 259-263.
71. Maccarone, E.; Mamo, A.; Torre, M. J. Org. Chem. 1979, 44, 1143-1145.
72. Sprinzak, Y. Org. Synth. Coll. Vol. IV 1963, 91-92.
73. Trifonov, L. S.; Orahovats, A. S. Helv. Chim. Acta 1987, 90, 1732-1736.
74. Okuda, S.; Robison, M. M. J. Org. Chem. 1959, 24, 1008-1011.
75. Wieland, H. Ber. Dtsch. Chem. Ges. 1920, 53, 1313-1328.
76. Hussein, F. A.; Kazandji, S. Y. J. Indian Chem. Soc. 1966, 43, 663-668.
77. Ullmann, F.; Jüngel, K. Ber. Dtsch. Chem. Ges. 1909, 42, 1077-1083.
78. Verardo, G.; Giumanini, A. G.; Favret, G.; Strazzolini, P. Synthesis 1991, 447-450.
79. Sznaidman, M. L.; Meade, E. A.; Beauchamp, L. M.; Russell, S.; Tisdale, M. Bioorg. Med. Chem. Lett. 1996, 6, 565-568.
80. Reddelien, G. Ber. Dtsch. Chem. Ges. 1914, 47, 1355-1364.
81. Elson, L. A.; Gibson, C. S. J. Chem. Soc. 1931, 2381-2388.
82. Kotsuki, H.; Kobayashi, S.; Matsumoto, K.; Suenaga, H.; Nishizawa, H. Synthesis 1990, 1147-1148.
83. Iter, J.; Casadevall, A. Bull. Chem. Soc. Fr. 1969, 2342-2355.
84. Gale, D. J.; Wilshire, J. F. Aust. J. Chem. 1972, 25, 2145-2154.
85. Legrand, L.; Lozac'h, N. Bull. Chem. Soc. Fr. 1969, 1173-1182.
86. Grigg, R.; Mitchell, T. R. B.; Tongpenyai, N. Synthesis 1981, 442-444.