AuI-catalyzed direct hydroamination/hydroarylation and double hydroamination of terminal alkynes

European Journal of Organic Chemistry

Volumn , Issue 24, 2010, Pages 4719-4731

  Patil, Nitin T ^a   Lakshmi, Pediredla G V V ^a   Singh, Vipender ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Alkynes; Cyclization; Gold catalysts; Heterocycles; Nucleophiles

Indexed keywords

EID: 77955704627     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201000389     Document Type: Article

References (130)

1. a) R. A. Sheldon, Pure Appl. Chem. 2000, 72, 1233-1246;
2. b) B. M. Trost, Science 1991, 254, 1471-1477;
3. c) B. M. Trost, Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
4. a) T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892;
5. R. Severin, S. Doye, Chem. Soc. Rev., 2007, 36, 1407-1420;
6. F. Pohlki, S. Doye, Chem. Soc. Rev. 2003, 32, 104-114;
7. F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079-3159;
8. e) M. Nobis, B. Drießen-Hölscher, Angew. Chem. Int. Ed. 2001, 40, 3983-3985;
9. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-704. For selected recent examples
10. see: g) H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100-12102;
11. X.-Y. Liu, C.-M. Che, Org. Lett. 2009, 11, 4204-4207;
12. X. Zeng, G. D. Frey, S. Kousar, G. Bertrand , Chem. Eur. J. 2009, 15, 3056-3060;
13. S. R. Beeren, S. L. Dabb, B. A. Messerle, J. Organomet. Chem., 2009, 694, 309-312;
14. J. M. Carney, P. J. Donoghue, W. M. Wuest, O. Wiest, P. Helquist, Org. Lett., 2008, 10, 3903-3906.
15. Reviews: a) S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673-686.
16. b) H. F. Yuen, T. J. Marks, Organometallics 2009, 28, 2423-2440;
17. c) A. Motta, I. L. Fragalà, T. J. Marks, Organometallics 2006, 25, 5533-5539;
18. H. Kim, T. Livinghouse, J. H. Shim, S. G. Lee, P. H. Lee, Adv. Synth. Catal., 2006, 348, 701-704.
19. For selected recent examples, see: a) H.-S. Yeom, E.-S. Lee, S. Shin, Synlett 2007, 2292-2294;
20. b) S. Ritter, Y. Horino, J. Lex, H.-G. Schmalz, Synlett 2006, 3309-3313;
21. c) D. Kadzimirsz, D. Hildebrandt, K. Merz, G. Dyker, Chem. Commun. 2006, 661-662;
22. S. L. Crawley, R. L. Funk, Org. Lett. 2006 8, 3995-3998;
23. B. C. J. V. Esseveldt, P. W. H. Vervoort, F. L. V. Delft, F. P. J. T. Rutjes, J. Org. Chem. 2005, 70, 1791-1795;
24. f) A. Antonio, B. Gabriele, M. Fabio, Synthesis 2004, 610-618;
25. E. Mizushima, T. Hayashi, M. Tanaka, Org. Lett. 2003, 5, 3349-3352.
26. a) L. Zhou, D. S. Bohle, H.-F. Jiang, C.-J. Li, Synlett 2009, 937-940;
27. b) X.-Y. Liu, C.-M. Che, Angew. Chem. Int. Ed. 2009, 48, 2367-2371;
28. c) K. Gräbe, B. Zwafelink, S. Doye, Eur. J. Org. Chem. 2009, 5565-5575;
29. K. Alex, A. Tillack, N. Schwarz, M. Beller, Org. Lett. 2008, 10, 2377-2379;
30. e) K. Alex, A. Tillack, N. Schwarz, M. Beller, Angew. Chem. Int. Ed. 2008, 47, 2304-2307;
31. X.-Y. Liu, P. Ding, J.-S. Huang, C.-M. Che, Org. Lett. 2007, 9, 2645-2649;
32. g) L. Ackermann, A. Althammer, Synlett 2006, 3125-3129;
33. h) C. Cao, Y. Li, Y. Shi, A. L. Odom, Chem. Commun. 2004, 2002-2003;
34. B. Ramanathan, A. J. Keith, D. Armstrong, A. L. Odom, Org. Lett. 2004, 6, 2957-2960;
35. j) H. Siebeneicher, I. Bytschkov, S. Doye, Angew. Chem. Int. Ed. 2003, 42, 3042-3044;
36. C. Cao, Y. Shi, A. L. Odom, Org. Lett. 2002, 4 2853-2856.
37. a) K. C. Nicolaou, J. S. Chen, Chem. Soc. Rev. 2009, 38, 2993-3009;
38. b) K. C. Nicolaou, D. J. Edmonds, P. G. Bulger, Angew. Chem. Int. Ed. 2006, 45, 7134-7186;
39. A. D. Meijere, P. V. Zezschwitz, S. Bräse, Acc. Chem. Res. 2005, 38, 413-422;
40. J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302-312;
41. e) A. Ajamian, J. L. Gleason, Angew. Chem. Int. Ed. 2004, 43, 3754-3760;
42. L. F. Tietze, Chem. Rev. 1996, 96, 115-136.
43. For selected recent reviews, see: a) A. Fürstner, Chem. Soc. Rev. 2009, 38, 3208-3221;
44. N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442;
45. c) S. F. Kirsch, Synthesis 2008, 3183-3204;
46. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378;
47. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265;
48. A. Arcadi, Chem. Rev. 2008, 108, 3266-3325;
49. g) N. Bongers, N. Krause, Angew. Chem. Int. Ed. 2008, 47, 2178-2181;
50. h) A. Fürstner, P. W. Davies, Angew. Chem. Int. Ed. 2007, 46, 3410-3449;
51. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211;
52. j) D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403;
53. k) E. Jiménez-Núñez, A. M. Echavarren, Chem. Commun. 2007, 333-346;
54. l) A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
55. m) S. Ma, S. Yu, Z. Gu, Angew. Chem. Int. Ed. 2006, 45, 200-203;
56. n) C. Nevado, A. M. Echavarren, Synthesis 2005, 167-182.
57. a) N. T. Patil, V. S. Raut, R. D. Kavthe, V. V. N. Reddy, P. V. K. Raju, Tetrahedron Lett. 2009, 50, 6576-6579;
58. F. J. Fañanás, A. Fernández., D. Cevic, F. Rodríguez, J. Org. Chem. 2009 74, 932-934;
59. S. Bhuvaneswari, M. Jeganmohan, C.-H. Cheng, Chem. Eur. J., 2007, 13, 8285-8293.
60. a) J. Barluenga, A. Fernández, A. Satrústegui, A. Diéguez, F. Rodríguez, F. J. Fañanás, Chem. Eur. J. 2008, 14, 4153-4156;
61. V. Belting, N. Krause, Org. Lett. 2006, 8, 4489-4492;
62. B. Liu, J. K. De Brabander, Org. Lett. 2006, 8, 4907-4910;
63. d) E. Genin, S. Antoniotti, V. Michelet, J.-P. Genêt, Angew. Chem. Int. Ed. 2005, 44, 4949-4953;
64. S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt, J. Am. Chem. Soc. 2005, 127, 9976-9977;
65. f) J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. Int. Ed. 1998, 37, 1415-1418.
66. a) J. Barluenga, A. Fernández, F. Rodríguez, F. J. Fañanás, J. Organomet. Chem. 2009, 694, 546-550;
67. C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358-1373;
68. c) A. S. K. Hashmi, M. C. Blanco, Eur. J. Org. Chem. 2006, 4340-4342;
69. T. Tsuchimoto, K. Hatanaka, E. Shirakawa, Y. Kawakami, Chem. Commun. 2003, 2454-2455.
70. E. Haak, I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2002, 457-463.
71. Also see:; A. V. Lee, L. L. Schafer, Synlett 2006, 2973-2976.
72. C. S. Yi, S. Y. Yun, J. Am. Chem. Soc. 2005, 127, 17000-17006.
73. a) M. E. Muratore, C. A. Holloway, A. W. Pilling, R. I. Storer, G. Trevitt, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 10796-10797;
74. T. Yang, L. Campbell, D. J. Dixon, J. Am. Chem. Soc. 2007, 129, 12070-12071.
75. J. Han, B. Xu, G. B. Hammond, J. Am. Chem. Soc. 2010, 132, 916-917.
76. N. T. Patil, R. D. Kavthe, V. S. Raut, V. S. Shinde, B. Sridhar, J. Org. Chem. 2010, 75, 1277-1280.
77. a) N. T. Patil, R. D. Kavthe, V. S. Shinde, B. Sridhar, J. Org. Chem. 2010, 75, ASAP;
78. N. T. Patil, R. D. Kavthe, V. S. Raut, V. V. N. Reddy, J. Org. Chem. 2009, 74, 6315-6318.
79. For syntheses and SAR studies of pyrrolo-quinoxalines, see: a) J. Guillon, S. Moreau, E. Mouray, V. Sinou, I. Forfar, S. B. Fabre, V. Desplat, P. Millet, D. Parzy, C. Jarry, P. Grellier, Bioorg. Med. Chem. 2008, 16, 9133-9144;
80. b) J. Guillon, I. Forfar, M. Mamani-Matsuda, V. Desplat, M. Saliège, D. Thiolat, S. Massip, A. Tabourier, J.-M. Léger, B. Dufaure, G. Haumont, C. Jarry, D. Mossalayi, Bioorg. Med. Chem. 2007, 15, 194-210;
81. c) J. Guillon, P. Grellier, M. Labaied, P. Sonnet, J.-M. Léger, R. Déprez-Poulain, I. Forfar-Bares, P. Dallemagne, N. Lemaître, F. Péhourcq, J. Rochette, C. Sergheraert, C. Jarry, J. Med. Chem. 2004, 47, 1997-2009;
82. K. Kobayashi, S. Irisawa, T. Matoba, T. Matsumoto, K. Yoneda, O. Morikawa, H. Konishi, Bull. Chem. Soc. Jpn. 2001, 74, 1109-1114;
83. M. Armengol, J. A. Joule, J. Chem. Soc. Perkin Trans. 1, 2001, 978-984;
84. J. Guillon, M. Boulouard, V. Lisowski, S. Stiebing, V. Lelong, P. Dallemagne, S. Rault, J. Pharm. Pharmacol. 2000, 52, 1369-1375;
85. g) J. Guillon, P. Dallemagne, B. Pfeiffer, P. Renard, D. Manechez, A. Kervran, S. Rault, Eur. J. Med. Chem. 1998, 33, 293-308;
86. h) H. Prunier, S. Rault, J.-C. Lancelot, M. Robba, P. Renard, P. Delagrange, B. Pfeiffer, D.-H. Caignard, R. Misslin, B. Guardiola-Lemaitre, M. Hamon, J. Med. Chem. 1997, 40, 1808-1819.
87. a) C. Meyers, G. Rombouts, K. T. J. Loones, A. Coelho, B. U. W. Maes, Adv. Synth. Catal. 2008, 350, 465-470;
88. K. Kobayashi, Y. Izumi, K. Hayashi, O. Morikawa, H. Konishi, Bull. Chem. Soc. Jpn. 2005, 78, 2171-2174;
89. c) Y.-L. Chen, C.-H. Chung, I.-L. Chen, P.-H. Chen, H.-Y. Jeng, Bioorg. Med. Chem. 2002, 10, 2705-2712;
90. d) P. Schmitt, C. H. Nguyen, J.-S. Sun, D. S. Grierson, E. Bisagni, T. Garestier, C. Hélène, Chem. Commun. 2000, 763-764;
91. M.-L. Go, T.-L. Ngiam, A. L.-C. Tan, K. Kuaha, P. Wilairat, Eur. J. Pharm. Sci. 1998 6, 19-26;
92. C. H. Nguyen, C. Marchand, S. Delage, J.-S. Sun, T. Garestier, C. Hélène, E. Bisagni, J. Am. Chem. Soc. 1998, 120, 2501-2507.
93. For syntheses and/or SAR studies of indoloquinoxalines, see: a) A. A. Mir, V. V. Mulwad, J. Chem. Res. 2009, 290-292;
94. b) G. Abbiati, E. M. Beccalli, G. Broggini, G. Paladino, E. Rossi, Synthesis 2005, 2881-2886;
95. M. S. Joseph, L. D. Basanagoudar, Synth. Commun. 2003, 33, 851-862;
96. d) A. Atfah, M. Y. Abu-Shuheil, J. Hill, H. Kotecha, J. Chem. Res. 1993, 52-53;
97. e) A. Atfah, Y. Abu-Shuheil, J. Hill, Tetrahedron 1990, 46, 6483-6500.
98. For reviews, see: a) S. B. Mhaske, N. P. Argade, Tetrahedron 2006, 62, 9787-9826;
99. b) L. Orfi, F. Waczek, J. Pato, I. Varga, B. Hegymegi-Barakonyi, R. A. Houghten, G. Ker, Curr. Med. Chem. 2004, 11, 2549-2553;
100. c) D. J. Connolly, D. Cusack, T. P. O'Sullivan, P. J. Guiry, Tetrahedron 2005, 61, 10153-10202;
101. J. P. Michael, Nat. Prod. Rep. 2007, 24, 223-246;
102. J. P. Michael, Nat. Prod. Rep. 2005, 22, 627-646;
103. J. P. Michael, Nat. Prod. Rep. 2004, 21, 650-668.
104. a) R. Rohini, K. Shanker, P. M. Reddy, Y.-P. Ho, V. Ravinder, Eur. J. Med. Chem. 2009, 44, 3330-3339;
105. b) S. Frère, V. Thiéry, C. Bailly, T. Besson, Tetrahedron 2003, 59, 773-779;
106. c) L. D. Via, O. Gia, S. M. Magno, A. D. Settimo, A. M. Marini, G. Primofiore, F. D. Settimo, S. Salerno, Farmaco 2001, 56, 159-167;
107. d) C. Lamazzi, S. Léonce, B. Pfeiffer, P. Renard, G. Guillaumet, C. W. Rees, T. Besson, Bioorg. Med. Chem. Lett. 2000, 10, 2183-2185;
108. M. F. Brana, J. M. Castellano, G. Keilhauer, A. Machuca, Y. Martin, C. Redondo, E. Schlick, N. Walker, Anticancer Res. 1994, 9, 527-538;
109. f) W. H. W. Lunn, R. W. Harper, R. L. Stone, J. Med. Chem. 1971, 14, 1069-1071.
110. Unlike in our previously reported case,[14,15] methanol is not a solvent of choice for the present transformation.
111. a) H. Duan, S. Sengupta, J. L. Petersen, N. G. Akhmedov, X. Shi, J. Am. Chem. Soc. 2009, 131, 12100-12102;
112. Y. Chen, W. Yan, N. G. Akhmedov, X. Shi, Org. Lett. 2010, 12, 344-347.
113. N. Marion, S. P. Nolan, Chem. Soc. Rev. 2008, 37, 1776-1782.
114. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136.
115. Y. Yamamoto, I. D. Gridnev, N. T. Patil, T. Jin, Chem. Commun. 2009, 5075-5087.
116. The reaction between 1a and 2d under the standard conditions afforded 3k in only 54% yield along with undesired side products obtained by the competing hydroamination/alkynylation/ hydroarylation cascade, see: a) Y. Zhou, E. Feng, G. Liu, D. Ye, J. Li, H. Jiang, H. Liu, J. Org. Chem. 2009, 74, 7344-7348;
117. b) X.-Y. Liu, C.-M. Che, Angew. Chem. Int. Ed. 2008, 47, 3805-3810.
118. It is interesting to note that N-vinylindole A was not obtained. For the synthesis of N-vinylindoles from o-alkynylamines, see: Y. Zhang, J. P. Donahue, C.-J. Li, Org. Lett. 2007, 9, 627-630.
119. For a review, see: J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020.
120. For selected reviews on microwave-assisted reactions in organic synthesis, see: a) P. Appukkuttan, V. P. Mehta, E. V. Van der Eycken, Chem. Soc. Rev. 2010, 39, 1467-1477;
121. C. O. Kappe, D. Dallinger, Mol. Divers. 2009, 13, 71-193;
122. c) P. Appukkuttan, E. V. Van der Eycken, Eur. J. Org. Chem. 2008, 1133-1155;
123. C. O. Kappe, Chem. Soc. Rev. 2008, 37, 1127-1139;
124. e) S. K. Das, Synlett 2004, 915-932;
125. A. de la Hoz, Á. Díaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164-178;
126. g) P. Lidström, J. Tierney, B. Wathey, J. Westmam, Tetrahedron 2001, 57, 9225-9283.
127. h) For a report on microwave-assisted alkyne hydroamination, see: I. Bytschkov, S. Doye, Eur. J. Org. Chem. 2001, 4411-4418.
128. The reaction between 1a and 2a in a preheated oil bath at 150 °C for 15 min gave 3a only in 10% yield.
129. H. L. Yale, M. Kankstein, J. Med. Chem. 1967, 10, 334-336.
130. V. B. Rao, C. V. Ratnam, Indian J. Chem., Sect. B 1977, 15, 1100-1102.