3-(o-Trifluoroacetamidoaryl)-1-propargylic esters: common intermediates for the palladium-catalyzed synthesis of 2-aminomethyl-, 2-vinylic, and 2-alkylindoles

Tetrahedron

Volumn 65, Issue 44, 2009, Pages 8916-8929

  Ambrogio, Ilaria ^a   Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Prastaro, Alessandro ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOMETHYLINDOLE DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 70349324514     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.113     Document Type: Article

References (77)

1. For some selected recent reviews, see:
2. Zeni G., and Larock R.C. Chem. Rev. 104 (2004) 2285
3. Alonso F., Beletskaya I.P., and Yus M. Chem. Rev. 104 (2004) 3079
4. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
5. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873
6. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875
7. Ackermann L. Synlett (2007) 5607
8. Krüger K., Tillack A., and Beller M. Adv. Synth. Catal. 350 (2008) 2153
9. Battistuzzi G., Cacchi S., and Fabrizi G. Eur. J. Org. Chem. (2002) 2671
10. For a review on the palladium-catalyzed reactions of propargylic esters, see:. Tsuji J., and Mandai T. Angew. Chem., Int. Ed. Engl. 34 (1995) 2589
11. Ambrogio I., Cacchi S., and Fabrizi G. Org. Lett. 10 (2006) 2083
12. Ambrogio I., Cacchi S., and Fabrizi G. Tetrahedron Lett. 48 (2007) 7721
13. Cacchi S., Fabrizi G., and Goggiamani A. Adv. Synth. Catal. 348 (2006) 1301 and the references cited therein
14. Tsutsumi K., Kawase T., Kakiuchi K., Ogoshi S., Okada Y., and Kurosawa H. Bull. Chem. Soc. Jpn. 72 (1999) 2687
15. Tsutsumi K., Yabukami T., Fujimoto K., Kawase T., Morimoto T., and Kakiuchi K. Organometallics 22 (2003) 2996
16. Korawa Y., and Mori M. J. Org. Chem. 68 (2003) 8068
17. Horton D.A., Bourne G.T., and Smythe M.L. Chem. Rev. 103 (2003) 893
18. For some recent selected references, see:
19. Hübner H., Gmeiner P., and Kraxner J. J. Med. Chem. 43 (2000) 4563
20. Clifford J.J., and Waddington J.L. Neuropsychopharmacol. 22 (2000) 538
21. Ortner B., Waibel R., and Gmeiner P. Angew. Chem., Int. Ed. 40 (2001) 1283
22. Moll A., Hübner H., Gmeiner P., and Troschutz R. Bioorg. Med. Chem. 10 (2002) 1671
23. Brioni, J. D.; Kolasa, T.; Hsieh, G. C.; Donnelly-Roberts, D. L. WO 2002041894, 2002;
24. Chem. Abstr. 136 (2002) 395987
25. Fliri, A. F. J.; Sanner, M. A.; Seymour, P. A.; Zorn, S. H. Eur. Patent 1177792, 2002;
26. Chem. Abstr. 136 (2002) 145264
27. Fliri, A. F. J.; Majchrzak, M. J.; Seymour, P. A.; Zorn, S. H.; Rollema, H. U.S. Patent 842,569, 2003;
28. Chem.Abstr. 138 (2003) 401610
29. Cowart M., Latshaw S.P., Bhatia P., Daanen J.F., Rohde J., Nelson S.L., Patel M., Kolasa T., Nakane M., Uchic M.E., Miller L.N., Terranova M.A., Chang R., Donnelly-Roberts D.L., Namovic M.T., Hollingsworth P.R., Martino B.R., Lynch III J.J., Sullivan J.P., Hsieh G.C., Moreland R.B., Brioni J.D.S., and Andrew O. J. Med. Chem. 47 (2004) 3853
30. Stewart A.O., Cowart M.D., Moreland R.B., Latshaw S.P., Matulenko M.A., Bhatia P.A., Wang X., Daanen J.F., Nelson S.L., Terranova M.A., Namovic M.T., Donnelly-Roberts D.L., Miller L.N., Nakane M., Sullivan J.P., and Brioni J.D. J. Med. Chem. 47 (2004) 2348
31. Tsuji J., Yamanaka T., Mitsumasa K., and Mandai T. Tetrahedron Lett. (1978) 2075
32. Trost B.M., Verhoeven T.R., and Fortunak J.M. Tetrahedron Lett. (1979) 2301
33. Laronze M., Boisbrun M., Leonce S., Pfeiffer B., Renard P., Lozach O., Meijer L., Lansiaux A., Bailly C., Sapi J., and Laronze J.-Y. Bioorg. Med. Chem. 13 (2005) 2263
34. Abbiati G., Canevari V., Facoetti D., and Rossi E. Eur. J. Org. Chem. (2007) 517
35. Nicolaou K.C., Dalby S.M., and Majumder U. J. Am. Chem. Soc. 130 (2008) 14942
36. Wang M., Gao M., Miller K.D., Sledge G.W., Hutchin G.D., and Zheng Q.-H. Eur. J. Med. Chem. 44 (2009) 2300
37. Katritzky A.R., and Akutagawa K. J. Am. Chem. Soc. 108 (1986) 6808
38. Inagaki S., Nishizawa Y., Sugiura T., and Ishihara H. J. Chem. Soc., Perkin Trans. 1 (1990) 179
39. Naruse Y., Ito Y., and Inagaki S. J. Org. Chem. 56 (1991) 2256
40. Rajeswaran W.G., and Srinivasan P.C. Indian J. Chem. 33B (1994) 368
41. For some selected examples, see:
42. Cadogan J.I.G., Cameron-Wood M., Mackie R.K., and Searle R.J.G. J. Chem. Soc. (1965) 4831
43. Sundberg R.J. J. Org. Chem. 30 (1965) 3604
44. Sundberg R.J., and Yamazaki T. J. Org. Chem. 32 (1967) 290
45. Levy A.B. J. Org. Chem. 43 (1978) 4684
46. Taylor E.C., Katz A.H., Salgado-Zamora H., and McKillop A. Tetrahedron Lett. 26 (1985) 5963
47. Gharpure M., Stoller A., Bellamy F., Firnau G., and Snieckus V. Synthesis (1991) 1079
48. Sadanandan E.V., and Srinivasan P.C. Synthesis (1992) 648
49. Mali R.S., Babu K.N., and Jagtap P. J. Chem. Res., Synop. (1995) 114
50. Wiedenau P., and Blechert S. Synth. Commun. 27 (1997) 2033
51. Taber D.F., and Tian W. J. Am. Chem. Soc. 128 (2006) 1058
52. Sanz R., Escribano J., Pedrosa M.R., Aguado R., and Arnáiz F.J. Adv. Synth. Catal. 349 (2007) 713
53. For a review, see:
54. Ragaini F., Cenini S., Gallo E., Caselli A., and Fantauzzi S. Curr. Org. Chem. 10 (2006) 1479
55. Andersson P.G., and Schab S. Organometallics 14 (1995) 1
56. Takacs J., Lawson E.C., and Clement F. J. Am. Chem. Soc. 119 (1997) 5956
57. Tsutsumi K., Ogoshi S., Nishiguchi S., and Kurosawa H. J. Am. Chem. Soc. 120 (1998) 1938
58. Baize M.W., Blosser P.W., Plantevin V., Schimpff D.G., Gallucci J.C., and Wojcicki A. Organometallics 15 (1996) 164
59. For some examples of reactions involving a nucleophilic attack at the central sp carbon of a σ-propargylpalladium complex to give a π-allylpalladium complex which is further attacked by a second nucleophile, see:
60. Fournier-Nguefack C., Lhoste P., and Sinou D. Synlett (1996) 553
61. Labrosse J.-R., Lhoste P., and Sinou D. Tetrahedron Lett. 40 (1999) 9025
62. Labrosse J.-R., Lhoste P., and Sinou D. Org. Lett. 2 (2000) 527
63. Yoshida M., Fujita M., Ishii T., and Ihara M. J. Am. Chem. Soc. 125 (2003) 4874
64. Yoshida M., Morishita Y., Fujita M., and Ihara M. Tetrahedron Lett. 45 (2004) 1861
65. Yoshida M., Morishita Y., Fujita M., and Ihara M. Tetrahedron 61 (2005) 4381
66. Duan X.-H., Guo L.-N., Bi H.-P., Liu X.-Y., and Liang Y.-M. Org. Lett. 8 (2006) 5777
67. Guo L.-Na., Duan X.-H., Bi H.-P., Liu X.-Y., and Liang Y.-M. J. Org. Chem. 72 (2007) 1538
68. Bi H.-P., Liu X.-Y., Gou F.-R., Guo L.-N., Duan X.-H., and Liang Y.-M. Org. Lett. 9 (2007) 3527
69. Bi H.-P., Guo L.-N., Gou F.-R., Duan X.-H., Liu X.-Y., and Liang Y.-M. J. Org. Chem. 73 (2008) 4713
70. Yoshida M., Higuchi M., and Shishido K. Tetrahedron Lett. 49 (2008) 1678
71. Tsuji J., and Yamakawa T. Tetrahedron Lett. (1979) 613
72. Tsuji J., Shimizu I., and Minami I. Chem. Lett. (1984) 1017
73. Tsuji J., Minami I., and Shimizu I. Synthesis (1986) 623
74. Hutchins R.O., and Learn K. J. Org. Chem. 47 (1982) 4380
75. See also:
76. Inomata K., and Kinoshita H. In: Negishi E. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 2 (2002), John Wiley & Sons, New York, NY 1887
77. Eitel M., and Pindur U. Synthesis (1989) 364