Palladium(II)/copper halide/solvent combination for selective intramolecular domino reactions of indolecarboxylic acid allylamides: An unprecedented arylation/esterification sequence

Advanced Synthesis and Catalysis

Volumn 354, Issue 1, 2012, Pages 159-170

  Broggini, Gianluigi ^a   Barbera, Vincenzina ^b   Beccalli, Egle M ^c   Borsini, Elena ^c   Galli, Simona ^a   Lanza, Giuseppe ^b   Zecchi, Gaetano ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

Copper; Domino reactions; Homogeneous catalysis; Palladium

Indexed keywords

EID: 84856819353     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100614     Document Type: Article

References (112)

1. For some general reviews, see: S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501;
2. Angew. Chem. Int. Ed. 2004, 43, 3400-3420;
3. E. M. Beccalli, G. Broggini, M. Martinelli, S. Sottocornola, Chem. Rev. 2007, 107, 5318-5365;
4. V. Kotov, C. C. Scarborough, S. S. Stahl, Inorg. Chem. 2007, 46, 1910-1923;
5. T. Jensen, P. Fristrup, Chem. Eur. J. 2009, 15, 9632-9636;
6. E. M. Beccalli, G. Broggini, A. Fasana, M. Rigamonti, J. Organomet. Chem. 2011, 696, 277-295;
7. J. Le Bras, J. Muzart, Chem. Rev. 2011, 111, 1170-1214;
8. R. I. McDonald, G. Liu, S. S. Stahl, Chem. Rev. 2011, 111, 2981-3019.
9. C. F. Rosewall, P. A. Sibbald, D. V. Liskin, F. E. Michael, J. Am. Chem. Soc. 2009, 131, 9488-9489;
10. C. E. Houlden, C. D. Bailey, J. Gair Ford, M. R. Gagn, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2008, 130, 10066-10067;
11. C. C. Scarborough, S. S. Stahl, Org. Lett. 2006, 8, 3251-3254
12. For some examples affording bicyclic compounds, see: K.-T. Yip, N.-Y. Zhu, D. Yang, Org. Lett. 2009, 11, 1911-1914;
13. B. Zhu, G.-W. Wang, Org. Lett. 2009, 11, 4334-4337;
14. K.-T. Yip, M. Yang, K.-L. Law, N.-Y. Zhu, D. Yang, J. Am. Chem. Soc. 2006, 128, 3130-3131;
15. P. Kubizna, I. Spanik, J. Kozisek, P. Szolcsanyi, Tetrahedron 2010, 66, 2351-2355.
16. For some examples of diamination reactions affording cyclization/ functionalization compounds, see: P. A. Sibbald, F. E. Michael, Org. Lett. 2009, 11, 1147-1149;
17. G. L. J. Bar, G. C. Lloyd-Jones, K. I. Booker-Milburn, J. Am. Chem. Soc. 2005, 127, 7308-7309
18. K. Muöiz, J. Streuff, P. Chvez, C. H. Hövelmann, Chem. Asian J. 2008, 3, 1248-1255;
19. K. Muöiz, C. H. Hövelmann, J. Streuff, J. Am. Chem. Soc. 2008, 130, 763-773;
20. T. Tsujihara, T. Shinohara, K. Takenaka, S. Takizawa, K. Onitsuka, M. Hatanaka, H. Sasai, J. Org. Chem. 2009, 74, 9274-9279;
21. C. H. Hövelmann, J. Streuff, L. Brelot, K. Muöiz, Chem. Commun. 2008, 2334-2336;
22. K. Muöiz, C. H. Hövelmann, E. Campos-Gomez, J. Barluenga, J. M. Gonzalez, J. Streuff, M. Nieger, Chem. Asian J. 2008, 3, 776-788;
23. J. Streuff, C. H. Hövelmann, M. Nieger, K. Muöiz, J. Am. Chem. Soc. 2005, 127, 14586-14587;
24. J. Alladoum, E. Vrancken, P. Mangeney, S. Roland, C. Kadouri-Puchot, Org. Lett. 2009, 11, 3746-3749;
25. K. Muöiz, J. Am. Chem. Soc. 2007, 129, 14542-14543.
26. For some examples of aminooxygenation reactions affording cyclization/functionalization compounds, see: E. J. Alexanian, C. Lee, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 7690-7691;
27. G. Liu, S. S. Stahl, J. Am. Chem. Soc. 2006, 128, 7179-7181;
28. E. Borsini, G. Broggini, A. Fasana, S. Galli, M. Khansaa, U. Piarulli, M. Rigamonti, Adv. Synth. Catal. 2011, 353, 985-994.
29. For some examples of aminohalogenation reactions affording cyclization/functionalization compounds, see: S. D. R. Christie, A. D. Warrington, C. J. Lunniss, Synthesis 2009, 148-154;
30. A. Lei, X. Lu, G. Liu, Tetrahedron Lett. 2004, 45, 1785-1788;
31. F. E. Michael, P. A. Sibbald, B. M. Cochran, Org. Lett. 2008, 10, 793-796;
32. M. R. Manzoni, T. P. Zabawa, D. Kasi, S. R. Chemler Organometallics 2004, 23, 5618-5621;
33. S. H. Kim H.-X. Wei, G. Li, Tetrahedron 2001, 57, 3869-3873;
34. Y.-N. Wang, A. Kattuboina, T. Ai, D. Banerjee, G. Li, Tetrahedron Lett. 2007, 48, 7894-7898;
35. E. Borsini, G. Broggini, F. Colombo, M. Khansaa, A. Fasana, S. Galli, D. Passarella, E. Riva, S. Riva, Tetrahedron: Asymmetry 2011, 22, 264-269.
36. R. J. Sundberg, Indoles; Academic Press, London, 1996;
37. A. Joule, Indole and its Derivatives in Science of Synthesis, in: Houben-Weyl Methods of Molecular Transformations, Vol. 10, (Ed.: E. J. Thomas), Thieme, Stuttgart, 2000; Chapter 10.13;
38. A. Kleeman, J. Engel, B. Kutscher, D. Reichert, Pharmaceutical Substances, 4th edn., Thieme, New York, 2001;
39. G. Karapetyan, K. Chakrabarty, M. Hein, P. Langer ChemMed-Chem 2011, 6, 25-37;
40. M. Ishikura, K. Yamada, T. Abe Nat. Prod. Rep. 2010, 27, 1630-1680;
41. T. L. Gilchrist, J. Chem. Soc. Perkin Trans. 1 1999, 2849-2866.
42. G. W. Gribble, J. Chem. Soc. Perkin Trans. 1 2000, 1045-1075;
43. R. Dalpozzo, G. Bartoli, Curr. Org. Chem. 2005, 9, 163-178;
44. S. Cacchi, G. Fabrizi, Chem. Rev. 2005, 105, 2873-2920;
45. G. W. Gribble, M. G. Saumier, E. T. Pelkey, T. L. S. Kishbaugh, Y. Liu, J. Jiang, H. A. Trujillo, D. J. Keavy, D. A. Davis, S. C. Conway, F. L. Switzer, S. Roy, R. A. Silva, J. A. Obaza-Nutatis, M. P. Sibi, N. V. Moskalev, T. C. Barden, L. Chang, W. M. Habeski, B. Pelcman, W. R. Sponholtz III, R. W. Chau, B. D. Allison, S. D. Garaas, M. S. Sinha, M. A. McGowan, M. R. Reese, K. S. Harpp, Curr. Org. Chem. 2005, 9, 1493-1519;
46. M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Synlett 2005, 1199-1222;
47. G. R. Humphrey, J. T. Kuethe, Chem. Rev. 2006, 106, 2875-2911;
48. J. Campo, M. Garca-Valverde, S. Marcaccini, M. J. Rojo, T. Torroba, Org. Biomol. Chem. 2006, 4, 757-765;
49. M. Bandini, A. Eichholzer, Angew. Chem. 2009, 121, 9786-9824
50. Angew. Chem. Int. Ed. 2009, 48, 9608-9644;
51. G. Bartoli, G. Bencivenni, R. Dalpozzo, Chem. Soc. Rev. 2010, 39, 4449-4465;
52. S. Cacchi, G. Fabrizi, A. Goggiamani, Org. Biomol. Chem. 2011, 9, 641-652;
53. P. A. Donets, E. V. Van der Eycken, Synthesis 2011, 2147-2153.
54. For a general review, see: E. M. Beck, M. J. Gaunt, Top. Curr. Chem. 2010, 292, 85-121. For some recent examples see:
55. C. Liu, R. A. Widenhoefer, Chem. Eur. J. 2006, 12, 2371-2382;
56. P. Y. Choy, C. P. Lau, F. Y. Kwong, J. Org. Chem. 2011, 76, 80-84;
57. A. Garcia-Rubia, B. Urones, R. Gomez Arrayas, J. C. Carretero, Chem. Eur. J. 2010, 16, 9676-9685;
58. Z. Shi, Y. Cui, N. Jiao, Org. Lett. 2010, 12, 2908-2911;
59. Y. Li, W.-H. Wang, S.-D. Yang, B.-J. Li, C. Feng, Z.-J. Shi, Chem. Commun. 2010, 4553-4555;
60. B. V. S. Reddy, Z Begum, Y. J. Reddy, J. S. Yadav, Tetrahedron Lett. 2010, 51, 3334-3336.
61. G. Broggini, G. Molteni, A. Terraneo, G. Zecchi, Heterocycles 2003, 59, 823-858;
62. E. M. Beccalli, G. Broggini, G. Paladino, A. Penoni, C. Zoni, J. Org. Chem. 2004, 69, 5627-5630;
63. E. M. Beccalli, G. Broggini, M. Martinelli, N. Masciocchi, S. Sottocornola, Org. Lett. 2006, 8, 4521-4524;
64. E. M. Beccalli, E. Borsini, G. Broggini, M. Rigamonti, S. Sottocornola, Synlett 2008, 1053-1057;
65. E. M. Beccalli, G. Broggini, F. Clerici, S. Galli, C. Kammerer, M. Rigamonti, S. Sottocornola, Org. Lett. 2009, 11, 1563-1566;
66. L. Basolo, E. M. Beccalli, E. Borsini, G. Broggini, Tetrahedron 2009, 65, 3486-3491;
67. A. M. Manzo, A. D. Perboni, G. Broggini, M. Rigamonti, Tetrahedron Lett. 2009, 50, 4696-4699;
68. E. M. Beccalli, E. Borsini, S. Brenna, S. Galli, M. Rigamonti, G. Broggini, Chem. Eur. J. 2010, 16, 1670-1678;
69. G. Broggini, E. M. Beccalli, E. Borsini, A. Fasana, G. Zecchi, Synlett 2011, 227-230;
70. A. M. Manzo, A. D. Perboni, G. Broggini, M. Rigamonti, Synthesis 2011, 127-132.
71. E. M. Beccalli, G. Broggini, C. La Rosa, D. Passarella, T. Pilati, A. Terraneo, G. Zecchi, J. Org. Chem. 2000, 65, 8924-8932;
72. E. M. Beccalli, G. Broggini, A. Marchesini, E. Rossi, Tetrahedron 2002, 58, 6673-6678;
73. E. M. Beccalli, G. Broggini, Tetrahedron Lett. 2003, 44, 1919-1921;
74. G. Abbiati, E. M. Beccalli, G. Broggini, C. Zoni, J. Org. Chem. 2003, 68, 7625-7628;
75. G. Abbiati, E. M. Beccalli, G. Broggini, G. Paladino, E. Rossi, Synthesis 2005, 2881-2886;
76. E. M. Beccalli, G. Broggini, M. Martinelli; G. Paladino, E. Rossi, Synthesis 2006, 2404-2412;
77. G. Abbiati, E. M. Beccalli, G. Broggini, M. Martinelli, G. Paladino, Synlett 2006, 73-76;
78. E. M. Beccalli, A. Bernasconi, E. Borsini, G. Broggini, M. Rigamonti, G. Zecchi, J. Org. Chem. 2010, 75, 6923-6932.
79. S. Chandrasekhar, N. K. Reddy, V. P. Kumar, Tetrahedron Lett. 2010, 51, 3623-3625;
80. P. Kubizna, I. Spanik, J. Kozisek, P. Szolcsanyi, Tetrahedron 2010, 66, 2351-2355;
81. M. Palk, O. Karlubkov, D. Lackovicov, A. Lsikov, T. Gracza, Tetrahedron 2010, 66, 5244-5249;
82. J.-M. Huang, Y. Dong, X.-X. Wang, H.-C. Luo, Chem. Commun. 2010, 1035-1037;
83. S. Ye, K. Gao, H. Zhou, X. Yang, J. Wu, Chem. Commun. 2009, 5406-5408;
84. S. Ma, B. Wu, X. Jiang, J. Org. Chem. 2005, 70, 2588-2593;
85. S. Ma, B. Wu, X. Jiang, S. Zhao, J. Org. Chem. 2005, 70, 2568-2575;
86. S. Ma, B. Wu, S. Zhao, Org. Lett. 2003, 5, 4429-4432;
87. Y. Li, K. J. Jardine, R. Tan, D. Song, V. M. Dong, Angew. Chem. 2009, 121, 9870-9872;
88. Angew. Chem. Int. Ed. 2009, 48, 9690-9692;
89. X. Han, X. Lu, Org. Lett. 2009, 11, 2381-2384.
90. H. Jiang, S. Ma, G. Zhu, X. Lu, Tetrahedron 1996, 52, 10945-10954;
91. J. Ji, X. Lu, Synlett 1993,745-747.
92. For the concept of transient palladium oxidation with CuCl2, see: H. Stangl, R. Jira, Tetrahedron Lett. 1970, 3589-3592;
93. O. Hamed, P. M. Henry, Organometallics 1998, 17, 5184-5189;
94. A. El-Qisairi, H. A. Qaseer, G. Katsigras, P. Lorenzi, U. Trivedi, S. Tracz, A. Hartman, J. A. Miller, P. M. Henry, Org. Lett. 2003, 5, 439-441.
95. For the concept of heterobimetallic s-Pd/Cu complex: P. Szolcsnyi, T. Gracza, Tetrahedron 2006, 62, 8498-8502;
96. P. Szolcsnyi, T. Gracza, Chem. Commun. 2005, 3948-3950;
97. T. Hosokawa, T. Uno, S. Inui, S.-I. Murahashi, J. Am. Chem. Soc. 1996, 118, 3990-3991.
98. T. W. Lyons, M. S. Sanford, Chem. Rev. 2010, 110, 1147-1169;
99. N. R. Deprez, M. S. Sanford, Inorg. Chem. 2007, 46, 1924-1935;
100. T. Tsujihara, K. Takenaka, K. Onitsuka, M. Hatanaka, H. Sasai, J. Am. Chem. Soc. 2009, 131, 3452-3453;
101. S. Nicolai, S. Erard, D. Fernandez Gonzalez, J. Waser, Org. Lett. 2010, 12, 384-387;
102. A. R. Dick, M. S. Remy, J. W. Kampf, M. S. Sanford, Organometallics 2007, 26, 1365-1370;
103. R. Giri; X. Chen; X. S. Hao; J. J. Li; J. Liang; Z. P. Fan; J. Q. Yu, Tetrahedron: Asymmetry 2005, 16, 3502-3505;
104. R. Giri; X. Chen; J. Q. Yu, Angew. Chem. 2005, 117, 2150-2153;
105. Angew. Chem. Int. Ed. 2005, 44, 2112-2115.
106. A. H. Jackson, P. Smith, J. Chem. Soc. Chem. Commun. 1967, 264-266;
107. A. H. Jackson, P. Smith, Tetrahedron 1968, 24, 403-413;
108. A. H. Jackson, P. Smith, Tetrahedron 1968, 24, 2227-2239;
109. A. Ganesan, C. H. Heathcock, Tetrahedron Lett. 1993, 34, 439-440;
110. C. Ferrer, C. H. M. Amijs, A. M. Echavarren, Chem. Eur. J. 2007, 13, 1358-1373.
111. E. Balogh-Hergovich, G. Speier, J. Chem. Soc. Perkin Trans. 1 1986, 2305-2308;
112. S. Tang, J.-H. Li, Y.-X. Xie, N.-X. Wang, Synthesis 2007, 1535-1541