Copper(I)-2-(2′-pyridyl)benzimidazole catalyzed N-arylation of indoles

Tetrahedron

Volumn 65, Issue 50, 2009, Pages 10459-10462

  Haneda, Satoshi ^a   Adachi, Yusuke ^a   Hayashi, Masahiko ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

Benzimidazole; Bidentate ligand; N arylation; Nitrogen ligand

Indexed keywords

1,10 PHENANTHROLINE; 2 (2' PYRIDYL)BENZIMIDAZOLE; 2,2' BIPYRIDINE; 5 (4 METHYLPHENOXY) 1H INDOLE; BENZIMIDAZOLE DERIVATIVE; CUPROUS ION; INDOLE DERIVATIVE; N (2 METHYLPHENYL)INDOLE; N (3 CHLOROPHENYL)INDOLE; N (4 CHLOROPHENYL)INDOLE; N (4 METHOXYPHENYL)INDOLE; N (4 METHYLPHENYL) 2 METHYLINDOLE; N (4 METHYLPHENYL) 2 PHENYLINDOLE; N (4 METHYLPHENYL) 3 METHYLINDOLE; N (4 METHYLPHENYL) 5 (4 METHYLPHENOXY)INDOLE; N (4 METHYLPHENYL) 5 AMINOINDOLE; N (4 METHYLPHENYL) 5 CHLOROINDOLE; N (4 METHYLPHENYL) 5 CYANOINDOLE; N (4 METHYLPHENYL) 5 METHOXYINDOLE; N (4 METHYLPHENYL) 5 METHYLINDOLE; N (4 METHYLPHENYL)INDOLE; N (4 METHYLPHENYL)METHYL INDOLE 3 CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE MEASUREMENT;

EID: 70350741918     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.014     Document Type: Article

References (78)

1. Kosugi M., Kameyama M., and Migita T. Chem. Lett. 12 (1983) 927-928
2. Guram A.S., Rennel R.A., and Buchwald S.L. Angew. Chem., Int. Ed. Engl. 34 (1995) 1348-1350
3. Louie J., and Hartwig J.F. Tetrahedron Lett. 36 (1995) 3609-3612
4. Nishiyama M., Yamamoto T., and Koike Y. Tetrahedron Lett. 39 (1998) 617-620
5. Review on the Pd-catalyzed amination. Hartwig J.F. Synlett (2006) 1283-1294
6. Haneda S., Ueba C., Eda K., and Hayashi M. Adv. Synth. Catal. 349 (2007) 833-835
7. Kawamura K., Haneda S., Gan Z., Eda K., and Hayashi M. Organometallics 27 (2008) 3748-3752
8. Haneda S., Gan Z., Eda K., and Hayashi M. Organometallics 26 (2007) 6551-6555
9. Other examples of nitrogen ligand-palladium catalyzed coupling reactions:
10. Cabri W., Candiani I., Bedeschi A., and Santi R. J. Org. Chem. 58 (1993) 7421-7426
11. Asselt R., and Elsevier C.J. Tetrahedron 50 (1994) 323-334
12. Done M.C., Rüther T., Cavell K.J., Kilner M., Peacock E.J., Braussaud N., Skelton B.W., and White A.H. J. Organomet. Chem. 607 (2000) 78-92
13. Rüther T., Done M.C., Cavell K.J., Peacock E.J., Skelton B.W., and White A.H. Organometallics 20 (2001) 5522-5531
14. Silberg J., Schareina T., Kempe R., Wurst K., and Buchmeiser M.R. J. Organomet. Chem. 622 (2001) 6-18
15. Buchmeiser M.R., Schareina T., Kempe R., and Wurst K. J. Organomet. Chem. 634 (2001) 39-46
16. Kawano T., Shinomaru T., and Ueda I. Org. Lett. 4 (2002) 2545-2547
17. Grasa G.A., Singh R., Stevens E.D., and Nolan S.P. J. Organomet. Chem. 687 (2003) 269-279
18. Nájera C., Gil-Moltó J., Karlström S., and Falvello L.R. Org. Lett. 5 (2003) 1451-1454
19. Iyer S., Kulkarni G.M., and Ramesh C. Tetrahedron 60 (2004) 2163-2172
20. Gupta A.K., Song C.H., and Oh C.H. Tetrahedron Lett. 45 (2004) 4113-4116
21. Reddy K.R., and Krishna G.G. Tetrahedron Lett. 46 (2005) 661-663
22. Cui X., Zhou Y., Wang N., Liu L., and Guo Q.-X. Tetrahedron Lett. 48 (2007) 163-167
23. Nitrogen monodentate-palladium catalyzed Mizoroki-Heck reactions:
24. Gossage R.A., Jenkins H.A., and Yadav P.N. Tetrahedron Lett. 45 (2004) 7689-7691
25. Eisnor C.R., Gossage R.A., and Yadav P.N. Tetrahedron 62 (2006) 3395-3401 and references cited therein
26. Klapars A., Antila J.C., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 123 (2001) 7727-7729
27. Klapars A., Huang X., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 7421-7428
28. Antila J.C., Klapars A., and Buchwald S.L. J. Am. Chem. Soc. 124 (2002) 11684-11688
29. Antila J.C., Baskin J.M., Barder T.E., and Buchwald S.L. J. Org. Chem. 69 (2004) 5578-5587
30. Kwong F.Y., Klapars A., and Buchwald S.L. Org. Lett. 4 (2002) 581-584
31. Job G.E., and Buchwald S.L. Org. Lett. 4 (2002) 3703-3706
32. Ma D., Zhang Y., Yao J., Wu S., and Tao F. J. Am. Chem. Soc. 120 (1998) 12459-12467
33. Ma D., and Xia C. Org. Lett. 3 (2001) 2583-2586
34. Ma D., Cai Q., and Zhang H. Org. Lett. 5 (2003) 2453-2455
35. Zhang H., Cai Q., and Ma D. J. Org. Chem. 70 (2005) 5164-5173
36. Zhu D., Xu L., Wu F., Mao J., and Wan B. Tetrahedron Lett. 47 (2006) 5781-5784
37. Xu L., Mao J., Zhu D., Wu F., Wang R., and Wan B. Tetrahedron 61 (2006) 6553-6560
38. Cristeau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Chem.-Eur. J. 10 (2004) 5607-5622
39. Cristeau H.-J., Cellier P.P., Spindler J.-F., and Taillefer M. Eur. J. Org. Chem. (2004) 695-700
40. Jiang Q., Jiang D., Jiang H., Fu H., and Zhao Y. Synlett (2007) 1836-1842
41. Shafir A., and Buchwald S.L. J. Am. Chem. Soc. 128 (2006) 8742-8743
42. de Lange B., Lambers-Verstappen M.H., de Schmieder-van Vondovoroort L., Sereinig N., Rijk R., de Vries A.H.M., and de Vries J.G. Synlett (2006) 3105-3109
43. Shafir A., Lichtor P.A., and Buchwald S.L. J. Am. Chem. Soc. 129 (2007) 3490-3491
44. Xia N., and Taillefer M. Angew. Chem., Int. Ed. 48 (2009) 337-339
45. Other ligands, see:
46. Lu Z., and Twieg R.J. Tetrahedron Lett. 46 (2005) 2997-3001
47. Rao H., Fu H., Jiang Y., and Zhao Y. J. Org. Chem. 70 (2005) 8107-8109
48. Zhu X., Ma Y., Su L., Song H., Chen G., Liang D., and Wan Y. Synthesis (2006) 3955-3962
49. Altman R.A., Koval E.D., and Buchwald S.L. J. Org. Chem. 72 (2007) 6190-6199
50. Rout L., Jammi S., and Punniyamurthy T. Org. Lett. 9 (2007) 3397-3399
51. Xu H., and Wolf C. Chem. Commun. (2009) 1715-1717
52. For reviews, see:
53. Hassan J., Sevignon M., Cozzi C., Schulz E., and Lamaire M. Chem. Rev. 102 (2002) 1359-1470
54. Ley S.V., and Thomas A.W. Angew. Chem., Int. Ed. 42 (2003) 5400-5449
55. Kunz K., Scholz U., and Ganzer D. Synlett (2003) 2428-2439
56. Beletskaya I.P., and Cheprakov A.V. Coord. Chem. Rev. 248 (2004) 2337-2364
57. Monnier F., and Tailefer M. Angew. Chem., Int. Ed. 47 (2008) 3096-3099
58. Evano G., Blanchard N., and Toumi M. Chem. Rev. 108 (2008) 3054-3131
59. For copper-catalyzed N-arylation of indoles:
60. 11(c);
61. 13(d);
62. Kantam M.L., Yadav J., Laha S., Sreedhar B., and Jha S. Adv. Synth. Catal. 349 (2007) 1938-1942
63. Periasamy M., Vairaprakash P., and Dalai M. Organometallics 27 (2008) 1963-1966
64. Tang B.-X., Guo S.-M., Zhang M.-B., and Li J.-H. Synthesis (2008) 1707-1716
65. Kawashita Y., Nakamichi N., Kawabata H., and Hayashi M. Org. Lett. 5 (2003) 3713-3716
66. Hayashi M. Chem. Rec. 8 (2008) 252-267
67. Naidu A.B., Raghunath O.R., Prasad D.J.C., and Sekar G. Tetrahedron Lett. 49 (2008) 1057-1061
68. Chang J.W.W., Chee S., Mak S., Buranaprasertsuk P., Chevasiri W., and Chan P.W.H. Tetrahedron Lett. 49 (2008) 2018-2022
69. Jammi S., Sakthivel S., Rout L., Mukherjee T., Mandal S., Mitra R., Saha P., and Punniyamurthy T. J. Org. Chem. 74 (2009) 1971-1976
70. 4).
71. Mino T., Harada Y., Shindo H., Sakamoto M., and Fujita T. Synlett (2008) 614-620
72. Nishio T. J. Org. Chem. 53 (1988) 1323-1326
73. Qi T., Qiu W., Liu Y., Zhang H., Gao X., Liu Y., Lu K., Du C., Yu G., and Zhu D. J. Org. Chem. 73 (2008) 4638-4643
74. Old D.W., Harris M.C., and Buchwald S.L. Org. Lett. 10 (2000) 1403-1406
75. Smith C.J., Tsang M.W.S., Holmes A.B., Danheiser R.L., and Tester J.W. Org. Biomol. Chem. 3 (2005) 3767-3781
76. Mao J., Guo J., Song H., and Ji S. Tetrahedron 64 (2008) 1383-1387
77. Zbiral E., and Drescher M. Synthesis (1998) 735-738
78. Kasper L.T., and Ackermann L. Tetrahedron (2005) 11311-11316