Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems

Organometallics

Volumn 21, Issue 14, 2002, Pages 2866-2873

  Grasa, Gabriela A ^a   Viciu, Mihai S ^a   Huang, Jinkun ^a   Zhang, Chunming ^a   Trudell, Mark L ^a   Nolan, Steven P ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS-COUPLING REACTIONS;

DRUG PRODUCTS; ELECTRONS; NITROGEN COMPOUNDS; PALLADIUM; SALTS; SYNTHESIS (CHEMICAL);

ORGANOMETALLICS;

EID: 0001388538     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020178p     Document Type: Article

References (90)

1. (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. (b) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Pinke, R. G. In Principles and Applications of Organotransition Metal Chemistry; University Science: Mill Valley, CA, 1987.
3. (c) Trost, B. M.; Verhoven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Vol. 8, pp 799-938.
4. (a) Roncali, J. J. Chem. Rev. 1992, 92, 711-738.
5. (b) Yamamura, K.; Ono, S.; Ogoshi, H.; Masuda, H.; Kuroda, Y. Synlett. 1989, 18-19.
6. (a) Torssell, K. G. B. Natural Product Chemistry; Wiley: Chichester, 1983.
7. (b) Thomson, R. H. The Chemistry of Natural Products; Blackie and Son: Glasgow, 1985.
8. (c) Huth, A.; Beetz, L; Schumann, I. Tetrahedron 1989, 45, 6679-6682.
9. (d) Ennis, D. S.; McManus, J.; Wood-Kaczmar, W.; Richardson, J.; Smith, G. E.; Crastairs, A. Org. Process Res. Dev. 1999, 3, 248-252.
10. (d) Baudoin, O.; Cesario, M.; Guenard Daniel; Gueritte, F. J. Org. Chem. 2002, 67, 1199-1207.
11. (a) For a review see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Suzuki, A. J. Organomet. Chem. 1999, 576 (1-2), 147-168.
12. (a) For a review see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. Suzuki, A. J. Organomet. Chem. 1999, 576 (1-2), 147-168.
13. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263-303.
14. (c) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 49-97, and references therein.
15. Herrmann, W. A.; Reisinger, C.-P.; Spiegler, M. J. Organomet. Chem, 1998, 557, 93-96.
16. (a) Yamamura, M.; Moritani, I.; Murahashi, S. J. Organomet. Chem. 1975, 91, C39.
17. (b) Tamao, K.; Kiso, Y.; Sumitani, K.; Kumada, M. J. Am. Chem. Soc. 1972, 94, 9268-9269.
18. (c) Sekia, A.; Ishikawa, N. J. Organomet. Chem. 1976, 118, 349-354.
19. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508-524.
20. (b) Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1986, 50, 1.
21. (c) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 167-202, and references therein.
22. (d) Handy, S. T.; Zhang X. Org. Lett. 2001, 3, 233-236.
23. Hatanaka, Y.; Hiyama, T. Synlett. 1991, 845-853.
24. Erdik, E. Tetrahedron 1992, 48, 9577-9648.
25. (a) Oh-e, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201-2208.
26. (b) Uenishi, J.; Beau, J.-M.; Armstrong, R. W.; Kishi, Y. J. Am. Chem. Soc. 1987, 109, 4756-4758.
27. (c) Uemura, M.; Nishimura, H.; Minami. T.; Hayashi, Y. J. Am. Chem. Soc. 1991, 113, 5402-5410.
28. Applications of phosphine ligands in homogeneous catalysis: (a) Parshall, G. W.; Ittel, S. Homogeneous Catalysis; J. Wiley and Sons: New York, 1992.
29. (b) Pignolet, L. H., Ed. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
30. (a) Littke, A. D.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020-4028, and references cited.
31. (b) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550-9561.
32. (c) Netherton, M. R.; Dai, C.; Neuschütz, K; Fu. G. C. J. Am. Chem. Soc. 2001, 123, 10099-10100.
33. (d) Yin, J.; Rainka, M. P.; Zhang, X.-X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 1162-1163.
34. (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
35. (b) Zim, D.; Gruber, A. S.; Ebeling, G.; Dupont, J.; Monteiro, A. L. Org. Lett. 2000, 2, 2881-2884.
36. (a) Regitz, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 725-728.
37. (b) Arduengo, A. J., III; Krafczyc, R. Chem. Zeit. 1998, 32, 6-14.
38. (c) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
39. Huang, J.; Schanz, H.-J.; Stevens, E. D.; Nolan, S. P. Organometallics 1999, 18, 2370-2375.
40. Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
41. Herrmann, W. A.; Goosen, L. T.; Köcher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805-2807.
42. Kücübay, H.; Cetinkaya, B.; Salaheddine, G.; Dixneuf, P. H. Organometallics 1996, 15, 2434-2439.
43. (a) Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
44. (b) Huang, J.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
45. (c) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
46. (d) Ackermann, L.; Fürstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790.
47. Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307-1309.
48. Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889-9890.
49. Lee, H.-M.; Nolan, S. P. Org. Lett. 2000, 2, 2053-2055.
50. Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119-122.
51. (a) Zhang, C.; Huang, J.; Trudell, M. T.; Nolan, S. P. J. Org. Chem. 1999, 64, 3804-3805.
52. (b) Böhm, V. P. W.; Gstöttmayr, C. W. K.; Weskamp, T.; Herrmann, W. A. J. Orgamomet. Chem. 2000, 595, 186-190.
53. (c) McGuiness, D.; Cavell, K. J. Organometallics 2000, 19, 741-748.
54. (d) Gstöttmayr, C. W. K.; Böhn, V. P. M.; Herdtweck, E.; Grosche, M.; Herrmann, W. A. Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
55. (a) Jafarpour, L.; Nolan, S. P. Adv. Organomet. Chem. 2000, 46, 181-222.
56. (b) Jafarpour, L.; Nolan, S. P. J. Organomet, Chem. 2001, 617, 17-27.
57. (c) Huang, J.; Jafarpour, L.; Hillier, A.; Stevens, E. D.; Nolan, S. P. Organometallics 2001, 20, 2878-2882, and references cited.
58. Littke, A. F.; Fu, G. C.Angew. Chem., Int. Ed. 1998, 37, 3387-3388.
59. Weissman, H.; Milstein, D. Chem. Commun. 1999, 1901-1902.
60. Suzuki, A. Pure Appl. Chem. 1994, 66, 213-222.
61. 2O/ IPr·HCl (3) has proven to be slower than the similar reaction of 4-chlorotoluene.
62. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000.
63. (a) Mathews, C. J.; Smith, P. J.; Welton, T.; White, A. J. P.; Williams, D. J. Organometallics 2001, 20, 3848-3850.
64. (b) Handy, T. H.; Zhang, X. Org. Lett. 2001, 3, 233-286.
65. (c) Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett. 1999, 1, 997-1000.
66. Xu, L.; Chen, W.; Xiao, J. Organometallics 2000, 19, 1123-1127, and references cited.
67. (a) Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033-3040.
68. (b) Rano, T. A.: Greenlee, M. L.; DeNino, F. P. Tetrahedron Lett. 1990, 31, 2853-2856.
69. Burini, A. A.; Cacohi, S.; Delmastro, M.; Marineli, F.; Pietroni, B. Synlett. 1990, 47-48.
70. Stang, P. J.; Hanack, M.; Subramanian, L. R. Synthesis 1982, 85-126.
71. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299-6302.
72. 4 as bases resulted in moderate yields.
73. (a) McGuiness, D. S.; Cavell, K. J.; Skelton, B. W.; White A. H. Organometallics 1999, 18, 1596-1605.
74. (b) Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-214.
75. (a) Lappert, M. F. J. Organomet. Chem. 1975, 100, 139-159.
76. (b) Schwarz, J.; Böhm, V. P. W.; Gardiner, M. G.; Grosche, M.; Hermann, W. A.; Hieringer, W.; Raudaschl-Sieber, G. Chem. Eur. J. 2000, 6, 1773-1780.
77. Farina, V.; Krishnan, B. J. Am. Chem. Soc. 1991, 113, 9585-9595.
78. Su, M.-D.; Chu, S.-Y. Inorg. Chem. 1988, 37, 3400-3406.
79. (a) Sakaki, S.; Biswas, B.; Sugimoto, M. Organometallics 1998, 17, 1278-1289.
80. (b) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158-1174.
81. Viciu, M. S.; Jafarpour, L.; Stevens, E. D.; Nolan, S. P. Manuscript in preparation.
82. (a) Jones, W. D.; Kuykendall, V. L. Inorg. Chem. 1991, 30, 2615-2622.
83. (b) Hartwig, J. F., Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626-3633
84. Vane, J. R. Nature 1971, 231, 232-235.
85. Duncia, J. V.; Chiu, A. T.; Carini, D. J.; Gregory, G. B.; Johnson, A. L.; Price, W. A.; Wells, G. J.; Wong, P. C.; Calabrese, J. C.; Timmermans, P. B. M. W. M. J. Med. Chem. 1990, 33, 1312-1329.
86. (a) Duncia, J. V.; Pierce, M. E.; Santella, J. B., III. J. Org. Chem. 1991, 56, 2395-2400.
87. (b) Duncia, J. V.; Carini, D. J.; Chiu, A. T.; Johnson, A. L.; Price, W. A.; Wong, P. C.; Wexler, R. R.; Timmermans, P. B. M. W. M. Med. Res. Rev. 1992, 12, 149-191.
88. Fu has also recently reported the synthesis of this strategic intermediate with a phosphine-modified palladium system; see ref 11a.
89. (a) Arduengo, A. J., III. US patent 5,077,414, 1991.
90. (b) Arduengo, A. J., III; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530-5534.