Directed palladation: Fine tuning permits the catalytic 2-alkenylation of indoles

Chemical Communications

Volumn , Issue 14, 2005, Pages 1854-1856

  Capito, Elena ^a,b   Brown, John M ^a   Ricci, Alfredo ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; INDOLE DERIVATIVE; PALLADIUM; RUTHENIUM COMPLEX;

ALKENYLATION; ARTICLE; ARYLATION; CARBONYLATION; CATALYSIS; CHEMICAL REACTION; COMPLEX FORMATION; COUPLING FACTOR; COVALENT BOND; HECK REACTION; REACTION ANALYSIS; STOICHIOMETRY;

EID: 17444430801     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417035k     Document Type: Article

References (27)

1. A. Jutand, Eur. J. Inorg. Chem., 2003, 2017-2040; C. Amatore and A. Jutand, Acc. Chem. Res., 2000, 33, 314-321; C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254-278.
2. A. Jutand, Eur. J. Inorg. Chem., 2003, 2017-2040; C. Amatore and A. Jutand, Acc. Chem. Res., 2000, 33, 314-321; C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254-278.
3. A. Jutand, Eur. J. Inorg. Chem., 2003, 2017-2040; C. Amatore and A. Jutand, Acc. Chem. Res., 2000, 33, 314-321; C. Amatore and A. Jutand, J. Organomet. Chem., 1999, 576, 254-278.
4. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
5. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
6. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
7. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
8. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
9. X. Du, M. Suguro, K. Hirabayashi, A. Mori, T. Nishikata, N. Hagiwara, K. Kawata, T. Okeda, H. F. Wang, K. Fugami and M. Kosugi, Org. Lett., 2001, 3, 3313-3316; M. M. S. Andappan, P. Nilsson and M. Larhed, Mol. Diversity, 2003, 7, 97-106; Y. C. Jung, R. K. Mishra, C. H. Yoon and K. W. Jung, Org. Lett., 2003, 5, 2231-2234; G. Zou, Z. Wang, J. Zhu and J. Tang, Chem. Commun., 2003, 2438-2439; M. M. S. Andappan, P. Nilsson and M. Larhed, Chem. Commun., 2004, 218-219; M. M. S. Andappan, P. Nilsson, H. von Schenck and M. Larhed, J. Org. Chem., 2004, 69, 5212-5218.
10. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries and P. W. N. M. van Leeuwen, J. Am. Chem. Soc., 2002, 124, 1586-1587; H. Horino and N. Inoue, J. Org. Chem., 1981, 46, 4416.
11. M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries and P. W. N. M. van Leeuwen, J. Am. Chem. Soc., 2002, 124, 1586-1587; H. Horino and N. Inoue, J. Org. Chem., 1981, 46, 4416.
12. C. Jia, T. Kitamura and Y. Fujiwara, Acc. Chem. Res., 2001, 34, 633-639.
13. F. Kakiuchi and S. Murai, Acc. Chem. Res., 2002, 35, 826-834.
14. B. S. Lane and D. Sames, Org. Lett., 2004, 6, 2897-2900; B. Sezen and D. Sames, J. Am. Chem. Soc., 2003, 125, 5274-5275; J. H. Smitrovich and I. W. Davies. Org. Lett., 2004, 6, 533-535.
15. B. S. Lane and D. Sames, Org. Lett., 2004, 6, 2897-2900; B. Sezen and D. Sames, J. Am. Chem. Soc., 2003, 125, 5274-5275; J. H. Smitrovich and I. W. Davies. Org. Lett., 2004, 6, 533-535.
16. B. S. Lane and D. Sames, Org. Lett., 2004, 6, 2897-2900; B. Sezen and D. Sames, J. Am. Chem. Soc., 2003, 125, 5274-5275; J. H. Smitrovich and I. W. Davies. Org. Lett., 2004, 6, 533-535.
17. T. Motoyama, Y. Shimazaki, T. Yajima, Y. Nakabayashi, Y. Naruta and O. Yamauchi, J. Am. Chen Soc., 2004, 126, 7378-7385; S. Tollari, F. Demartin, S. Cenini, G. Palmisano and P. Raimondi, J. Organomet. Chem., 1997, 527, 93-102.
18. T. Motoyama, Y. Shimazaki, T. Yajima, Y. Nakabayashi, Y. Naruta and O. Yamauchi, J. Am. Chen Soc., 2004, 126, 7378-7385; S. Tollari, F. Demartin, S. Cenini, G. Palmisano and P. Raimondi, J. Organomet. Chem., 1997, 527, 93-102.
19. R. Cooper, A. R. Cowley, E. Capito, J. M. Brown and A. Ricci, Acta Crystallogr. Sect. E, submitted.
20. M. Nonoyama, J. Organomet. Chem., 1984, 262, 407-412; M. Nonoyama, Trans. Met. Chem., 1987, 12, 1-3; M. Nonoyama and K. Nakajima, Polyhedron, 1998, 18, 533-543.
21. M. Nonoyama, J. Organomet. Chem., 1984, 262, 407-412; M. Nonoyama, Trans. Met. Chem., 1987, 12, 1-3; M. Nonoyama and K. Nakajima, Polyhedron, 1998, 18, 533-543.
22. M. Nonoyama, J. Organomet. Chem., 1984, 262, 407-412; M. Nonoyama, Trans. Met. Chem., 1987, 12, 1-3; M. Nonoyama and K. Nakajima, Polyhedron, 1998, 18, 533-543.
23. W. A. Herrmann, C. Brossmer, C. P. Reisinger, T. H. Riermeier, K. Ofele and M. Beller, Chem. Eur. J., 1997, 3, 1357-1364.
24. I. P. Smoliakova, K. J. Keuseman, D. C. Haagenson, D. M. Wellmann, P. B. Colligan, N. A. Kataeva, A. V. Churakov, L. G. Kuz'mina and V. V. Dunina, J. Organomet. Chem., 2000, 603, 86-97 for a simple arene analogue.
25. Y. Yokoyama, K. Tsuruta and Y. Murakami, Heterocycles, 2002, 56, 525-529; Y. Murakami, Y. Yokoyama and T. Aoki, Heterocycles, 1984, 22, 1493-1496.
26. Y. Yokoyama, K. Tsuruta and Y. Murakami, Heterocycles, 2002, 56, 525-529; Y. Murakami, Y. Yokoyama and T. Aoki, Heterocycles, 1984, 22, 1493-1496.
27. G. Abbiati, E. M. Beccalli, G. Broggini and C. Zoni, J. Org. Chem., 2003, 68, 76.