Gold(I)-catalyzed one-pot reaction between 2-alkynylanilines and alkynols leading to the formation of C-3-substituted indoles: a case of formal carboamination of alkynes

Tetrahedron Letters

Volumn 51, Issue 11, 2010, Pages 1493-1496

  Patil, Nitin T ^a   Singh, Vipender ^a   Konala, Ashok ^a   Mutyala, Anil Kumar ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkynes; Gold catalyst; Hydroalkoxylation; Hydroamination; Hydroarylation

Indexed keywords

2 ANILINE; 2 ETHYNYLANILINE; ANILINE DERIVATIVE; GOLD; SILVER; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; ARYLATION; CATALYSIS; CATALYST; CHEMICAL REACTION; ONE POT SYNTHESIS; QUANTUM YIELD;

EID: 75749100271     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.01.036     Document Type: Article

References (83)

1. Li S.-M. Nat. Prod. Rep. 27 (2010) 57-78
2. Weng J.-R., Tsai C.-H., Kulp S.K., and Chen C.-S. Cancer Lett. 262 (2008) 153-163
3. Rieck G.C., and Fiander A.N. Mol. Nutr. Food Res. 52 (2008) 105-113
4. Brancale A., and Silvestri R. Med. Res. Rev. 27 (2007) 209-238
5. Somei M., and Yamada F. Nat. Prod. Rep. 22 (2005) 73-103
6. McKay M.J., Carroll A.R., Quinn R.J., and Hooper J.N.A. J. Nat. Prod. 65 (2002) 595-597
7. Joule J.A., and Mills K. Heterocyclic Chemistry. fourth ed. (2000), Blackwell Science, Oxford
8. Sundberg R.J. Indoles (1996), Academic Press, London
9. Reviews:. Ackermann L. Synlett (2007) 507-526
10. Humphrey G.R., and Kuethe J.T. Chem. Rev. 106 (2006) 2875-2911
11. Bandini M., Melloni A., Tommasi S., and Umani-Ronchi A. Synlett (2005) 1199-1222
12. Gribble G.W. J. Chem. Soc., Perkin Trans. 1 (2000) 1045-1075
13. Review:. Krügar K., Tillack A., and Beller M. Adv. Synth. Catal. 350 (2008) 2153-2167
14. Cacchi S., and Fabrizi G. Chem. Rev. 105 (2005) 2873-2920
15. In: Li J.J., and Gribble W. (Eds). Palladium in Heterocyclic Chemistry (2000), Pergamon, Oxford Chapter 3
16. For recent references on synthesis of indoles by metal catalysis, see:. Hsieh T.H.H., and Dong V.M. Tetrahedron 65 (2009) 3062-3068
17. Stuart D.R., Bertrand-Laperle M., Burgess K.M.N., and Fagnou K. J. Am. Chem. Soc. 130 (2008) 16474-16475
18. Banerjee S., Barnea E., and Odom A.L. Organometallics 27 (2008) 1005-1014
19. Alex K., Tillack A., Schwarz N., and Beller M. Angew. Chem., Int. Ed. 47 (2008) 2304-2307
20. Kurisaki T., Naniwa T., Yamamoto H., Imagawa H., and Nishizawa M. Tetrahedron Lett. 48 (2007) 1871-1874
21. Liu F., and Ma D. J. Org. Chem. 72 (2007) 4844-4850
22. Ohno H., Ohta Y., Oishi S., and Fujii N. Angew. Chem., Int. Ed. 46 (2007) 2295-2298
23. Cariou K., Ronan B., Mignani S., Fensterbank L., and Malacria M. Angew. Chem., Int. Ed. 46 (2007) 1881-1884
24. Kamijo S., and Yamamoto Y. Angew. Chem., Int. Ed. 41 (2002) 3230-3233
25. Kamijo S., and Yamamoto Y. J. Am. Chem. Soc. 124 (2002) 11940-11945
26. For metal catalyzed hydroamination of 2-alkynylanilines, see:. Okuma K., Seto J., Sakaguchi K., Ozaki S., Nagahora N., and Shioji K. Tetrahedron Lett. 50 (2009) 2943-2945
27. Sakai N., Annaka K., Fujita A., Sato A., and Konakahara T. J. Org. Chem. 73 (2008) 4160-4165
28. Zhang Y., Donahue J.P., and Li C.-J. Org. Lett. 9 (2007) 627-630
29. Ambrogio I., Arcadi A., Cacchi S., Fabrizi G., and Marinelli F. Synlett (2007) 1775-1779
30. Trost B.M., and McClory A. Angew. Chem., Int. Ed. 46 (2007) 2074-2077
31. Li X., Chianese A.R., Vogel T., and Crabtree R.H. Org. Lett. 7 (2005) 5437-5440
32. Alfonsi M., Arcadi A., Aschi M., Bianchi G., and Marinelli F. J. Org. Chem. 70 (2005) 2265-2273
33. Hiroya K., Itoh S., and Sakamoto T. Tetrahedron 61 (2005) 10958-10964
34. Hiroya K., Itoh S., and Sakamoto T. J. Org. Chem. 69 (2004) 1126-1136
35. Sakai N., Annaka K., and Konakahara T. Org. Lett. 6 (2004) 1527-1530
36. Arcadi A., Bianchi G., and Merinelli F. Synthesis (2004) 610-618
37. Hiroya K., Itoh S., Ozawa M., Kanamori Y., and Sakamoto T. Tetrahedron Lett. 43 (2002) 1277-1280
38. Kondo T., Okada T., Suzuki T., and Mitsudo T. J. Organomet. Chem. 622 (2001) 149-154
39. Cacchi S., Carnicelli V., and Marinelli F. J. Organomet. Chem. 475 (1994) 289-296
40. McDonald F.E., and Chatterjee A.K. Tetrahedron Lett. 38 (1997) 7687-7690
41. Arcadi A., Cacchi S., and Marinelli F. Tetrahedron Lett. 30 (1989) 2581-2584
42. Rudisill D.E., and Stille J.K. J. Org. Chem. 54 (1989) 5856-5866
43. Iritani K., Matsubara S., and Utimoto K. Tetrahedron Lett. 29 (1988) 1799-1802
44. Nakamura I., Sato Y., Konta S., and Terada M. Tetrahedron Lett. 50 (2009) 2075-2077
45. Fürstner A., and Davies P.W. J. Am. Chem. Soc. 127 (2005) 15024-15025
46. Shimada T., Nakamura I., and Yamamoto Y. J. Am. Chem. Soc. 126 (2004) 10546-10547
47. Cacchi S., Fabrizi G., and Pace P. J. Org. Chem. 63 (1998) 1001-1011
48. Patil N.T., Raut V.S., Kavthe R.D., Reddy V.V.N., and Raju P.V.K. Tetrahedron Lett. 50 (2009) 6576-6579
49. Barluenga J., Fernández A., Rodríguez F., and Fañanás F.J. J. Organomet. Chem. 694 (2009) 546-550
50. Bhuvaneswari S., Jeganmohan M., and Cheng C.-H. Chem. Eur. J. 13 (2007) 8285-8293
51. Ferrer C., Amijs C.H.M., and Echavarren A.M. Chem. Eur. J. 13 (2007) 1358-1373
52. Li X., Wang J.-Y., Yu W., and Wu L.-M. Tetrahedron 65 (2009) 1140-1146
53. Selected recent reviews:. Fürstner A. Chem. Soc. Rev. 38 (2009) 3208-3221
54. Patil N.T., and Yamamoto Y. Chem. Rev. 108 (2008) 3395-3442
55. Kirsch S.F. Synthesis (2008) 3183-3204
56. Gorin D.J., Sherry B.D., and Toste F.D. Chem. Rev. 108 (2008) 3351-3378
57. Li Z., Brouwer C., and He C. Chem. Rev. 108 (2008) 3239-3265
58. Arcadi A. Chem. Rev. 108 (2008) 3266-3325
59. Bongers N., and Krause N. Angew. Chem., Int. Ed. 47 (2008) 2178-2181
60. Fürstner A., and Davies P.W. Angew. Chem., Int. Ed. 46 (2007) 3410-3449
61. Hashmi A.S.K. Chem. Rev. 107 (2007) 3180-3211
62. Gorin D.J., and Toste F.D. Nature 446 (2007) 395-403
63. Jiménez-Núñez E., and Echavarren A.M. Chem. Commun. (2007) 333-346
64. Hashmi A.S.K., and Hutchings G.J. Angew. Chem., Int. Ed. 45 (2006) 7896-7936
65. Ma S., Yu S., and Gu Z. Angew. Chem., Int. Ed. 45 (2006) 200-203
66. Nevado C., and Echavarren A.M. Synthesis (2005) 167-182
67. Wasilke J.-C., Obrey S.J., Baker R.T., and Bazan G.C. Chem. Rev. 105 (2005) 1001-1020
68. Report on formal processes from our laboratory, see:. Patil N.T., Kavthe R.D., Raut V.S., and Reddy V.V.N. J. Org. Chem. 74 (2009) 6315-6318
69. Ref. 6.
70. 3)Cl/Ag(OTf) (5 mol % each with respect to 2) in DCE (0.3 M). The reaction vial was fitted with a cap, evacuated, and filled with nitrogen. The reaction vial was heated with stirring at 60 °C for the specified time. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate, and filtered through a plug of silica gel. The filtrate was concentrated and the residue thus obtained was purified by silica gel column chromatography using hexane and ethyl acetate as an eluent. The details are given in the Supplementary data.
71. Hashmi A.S.K., Schuster A.M., and Rominger F. Angew. Chem., Int. Ed. 48 (2009) 8247-8249
72. For metal catalyzed hydroalkoxylation of alkynes, see:. Harkat H., Blanc A., Weibel J.-M., and Pale P. J. Org. Chem. 73 (2008) 1620-1623
73. Harkat H., Weibel J.-M., and Pale P. Tetrahedron Lett. 48 (2007) 1439-1442
74. Barluenga J., Diéguez A., Rodríguez F., Fañanás F.J., Sordo T., and Campomanes P. Chem. Eur. J. 11 (2005) 5735-5741
75. Peng A.-Y., and Ding Y.-X. Org. Lett. 7 (2005) 3299-3301
76. Liu Y., Song F., Song Z., Liu M., and Yan B. Org. Lett. 7 (2005) 5409-5412
77. Peng A.-Y., and Ding Y.-X. J. Am. Chem. Soc. 125 (2003) 15006-15007
78. Pale P., and Chuche J. Eur. J. Org. Chem. (2000) 1019-1025
79. BEMP has previously been used as nonpoisoning proton scavenger, see:. Barluenga J., Fernández A., Diéguez A., Rodríguez F., and Fañanás F.J. Chem. Eur. J. 15 (2009) 11660-11667
80. Yang T., Campbell L., and Dixon D.J. J. Am. Chem. Soc. 129 (2007) 12070-12071
81. Reviews on atom economy:. Sheldon R.A. Pure Appl. Chem. 72 (2000) 1233-1246
82. Trost B.M. Science 254 (1991) 1471-1477
83. Trost B.M. Angew. Chem., Int. Ed. 34 (1995) 259-281