Sequential homobimetallic catalysis: An unprecedented tandem Pd(0)-catalysed deprotection - Pd(II)-catalysed heterocyclisation reaction leading to benzofurans

Chemical Communications

Volumn , Issue 2, 2005, Pages 271-273

  Gabriele, Bartolo ^a   Mancuso, Raffaella ^a   Salerno, Giuseppe ^a   Veltri, Lucia ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; PALLADIUM; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CYCLIZATION; DEPROTECTION REACTION; OXIDATION; REACTION ANALYSIS;

EID: 12744274567     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b413240h     Document Type: Article

References (20)

1. 2-(1-Hydroxyalk-2-ynyl)phenols, with the -OH group unprotected, could not be prepared and used directly as substrates because of their instability, according to the literature: D. Pflieger and B. Muckensturm, Tetrahedron Lett., 1990, 31, 2299.
2. 2 in conjunction with an excess of KI as the catalytic system for carbonylation reactions was disclosed by us several years ago: B. Gabriele, M. Costa, G. Salerno and G. P. Chiusoli, Chem. Commun., 1992, 1007; B. Gabriele, M. Costa, G. Salerno and G. P. Chiusoli, J. Chem. Soc., Perkin Trans. 1, 1994, 83.
3. 2 in conjunction with an excess of KI as the catalytic system for carbonylation reactions was disclosed by us several years ago: B. Gabriele, M. Costa, G. Salerno and G. P. Chiusoli, Chem. Commun., 1992, 1007; B. Gabriele, M. Costa, G. Salerno and G. P. Chiusoli, J. Chem. Soc., Perkin Trans. 1, 1994, 83.
4. J. Tsuji and T. Mandai, J. Organomet. Chem., 1993, 451, 15 and references therein.
5. The Pd(0) catalysed substitutive carbonylation of allylic derivatives is a well-known reaction: J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995, pp. 340-345; T. Mandia, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed. E. Negishi, Wiley-InterScience, New York, 2002, vol. 2, pp. 2505-2508.
6. The Pd(0) catalysed substitutive carbonylation of allylic derivatives is a well-known reaction: J. Tsuji, Palladium Reagents and Catalysts, John Wiley & Sons, Chichester, 1995, pp. 340-345; T. Mandia, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed. E. Negishi, Wiley-InterScience, New York, 2002, vol. 2, pp. 2505-2508.
7. For very recent reviews and accounts on this kind of reactivity, see: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Organomet. Chem., 2003, 687, 219; B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, Curr. Org. Chem., 2004, 8, 919; F. Alonso, I. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079; S. A. Vizer, K. B. Yerzhanov, A. A. A. Al Quntar and V. M. Vembitsky, Tetrahedron, 2004, 60, 5499.
8. For very recent reviews and accounts on this kind of reactivity, see: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Organomet. Chem., 2003, 687, 219; B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, Curr. Org. Chem., 2004, 8, 919; F. Alonso, I. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079; S. A. Vizer, K. B. Yerzhanov, A. A. A. Al Quntar and V. M. Vembitsky, Tetrahedron, 2004, 60, 5499.
9. For very recent reviews and accounts on this kind of reactivity, see: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Organomet. Chem., 2003, 687, 219; B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, Curr. Org. Chem., 2004, 8, 919; F. Alonso, I. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079; S. A. Vizer, K. B. Yerzhanov, A. A. A. Al Quntar and V. M. Vembitsky, Tetrahedron, 2004, 60, 5499.
10. For very recent reviews and accounts on this kind of reactivity, see: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Organomet. Chem., 2003, 687, 219; B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, Curr. Org. Chem., 2004, 8, 919; F. Alonso, I. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079; S. A. Vizer, K. B. Yerzhanov, A. A. A. Al Quntar and V. M. Vembitsky, Tetrahedron, 2004, 60, 5499.
11. The possibility of obtaining a π-allylpalladium complex directly from the reaction between an allyl alcohol and a palladium hydride species without any activator was disclosed by us some years ago: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Mol. Catal., 1996, 111, 43. More recently, the formation of an allylpalladium intermediate from allyl alcohols and an hydridopalladium complex has been reported: F. Ozawa, T. Ishiyama, S. Yamamoto, S. Kawagishi and H. Murakami, Organometallics, 2004, 23, 1698.
12. The possibility of obtaining a π-allylpalladium complex directly from the reaction between an allyl alcohol and a palladium hydride species without any activator was disclosed by us some years ago: B. Gabriele, G. Salerno, M. Costa and G. P. Chiusoli, J. Mol. Catal., 1996, 111, 43. More recently, the formation of an allylpalladium intermediate from allyl alcohols and an hydridopalladium complex has been reported: F. Ozawa, T. Ishiyama, S. Yamamoto, S. Kawagishi and H. Murakami, Organometallics, 2004, 23, 1698.
13. The possibility of reducing an allyl alcohol moiety through the reaction with an H-Pd-I species with formation of a π-allyl complex followed by protonolysis has been recently demonstrated by us: G. P. Chiusoli, M. Costa, L. Cucchia, B. Gabriele, G. Salerno and L. Veltri, J. Mol. Catal. A: Chem., 2003, 687, 219.
14. B. Gabriele, L. Veltri, G. Salerno, M. Costa and G. P. Chiusoli, Eur. J. Org. Chem., 2003, 1722 and references therein.
15. 2H complexes to give X-Pd-H species is a well-known process: see, for example, references 6, 7 and R. Bertani, G. Cavinato, L. Toniolo and G. Vasapollo, J. Mol. Catal., 1993, 84, 165; V. V. Grushin, Chem. Rev., 1996, 96, 2011.
16. 2H complexes to give X-Pd-H species is a well-known process: see, for example, references 6, 7 and R. Bertani, G. Cavinato, L. Toniolo and G. Vasapollo, J. Mol. Catal., 1993, 84, 165; V. V. Grushin, Chem. Rev., 1996, 96, 2011.
17. 2C=CMgBr.
18. For some very recent examples, see: E. Tsuji, K. Ando, J. Kunitomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2003, 1, 3139; K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka and N. Shimma, Bioorg. Med. Chem. Lett., 2003, 13, 87.
19. For some very recent examples, see: E. Tsuji, K. Ando, J. Kunitomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2003, 1, 3139; K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, Y. Shiratori, Y. Aoki, T. Ohtsuka and N. Shimma, Bioorg. Med. Chem. Lett., 2003, 13, 87.
20. T. N. Wheeler (Union Carbide Corp., USA), US Pat. 4,431,650, 1977 (Chem. Abstr. 1984, 101, 54903u).