An N-C-N pincer palladium complex as an efficient catalyst precursor for the Heck reaction

Advanced Synthesis and Catalysis

Volumn 346, Issue 13-15, 2004, Pages 1693-1696

  Takenaka, Kazuhiro ^a   Uozumi, Yasuhiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

Aryl halides; Cinnamates; Heck reaction; Palladacycle catalyst; Pincer complex

Indexed keywords

[4 TERT BUTYL 2,6 BIS(2 PHENYLHEXAHYDRO 1H PYRROLO[1,2 C]IMIDAZOL 1 ON 3 YL)PHENYL]CHLOROPALLADIUM; ACRYLIC ACID METHYL ESTER; CINNAMIC ACID DERIVATIVE; CINNAMIC ACID METHYL ESTER; IODOBENZENE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; HECK REACTION; PRECURSOR; REACTION ANALYSIS; TEMPERATURE; TIME;

EID: 12344261609     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404161     Document Type: Article

References (28)

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5. For reviews on pincer complexes, see: a) M. Albrecht, G. van Koten, Angew. Chem. Int. Ed. 2001, 40, 3750; b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759; c) J. T. Singleton, Tetrahedron 2003, 59, 1837.
6. For reviews on pincer complexes, see: a) M. Albrecht, G. van Koten, Angew. Chem. Int. Ed. 2001, 40, 3750; b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759; c) J. T. Singleton, Tetrahedron 2003, 59, 1837.
7. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
8. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
9. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
10. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
11. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
12. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
13. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
14. For recent studies on the Heck reaction with pincer catalysts, see: a) I. G. Jung, S. U. Son, K. H. Park, K.-C. Chung, J. W. Lee, Y. K. Chung, Organometallics 2003, 22, 4715; b) E. Díez-Barra, J. Guerra, V. Hornillos, S. Merino, J. Tejeda, Organometallics 2003, 22, 4610; c) F. Miyazaki, K. Yamaguchi, M. Shibasaki, Tetrahedron Lett. 1999, 40, 7379; d) D. Morales-Morales, R. Redón, C. Yung, C. M. Jensen, Chem. Commun. 2000, 1619; e) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687; f) D. E. Bergbreiter, P. L. Osburn, Y.-S. Liu, J. Am. Chem. Soc. 1999, 121, 9531; g) A. S. Gruber, D. Zim, G. Ebeling, A. L. Monteiro, J. Dupont, Org. Lett. 2000, 2, 1287; h) S. Sjövall, O. F. Wendt, C. Andersson, J. Chem. Soc. Dalton Trans. 2002, 1396; i) M.-H. Huang, L.-C. Liang, Organometallics 2004, 23, 2813.
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21. It has recently been reported that palladium nanoparticles and/or low ligated palladium species are generated in situ from carbopalladacycle complexes to exhibit the extraordinarily high catalytic performance in the Heck reaction; see: a) M. Nowotny, U. Hanefeld, H. van Koningsveld, T. Maschmeyer, Chem. Commun. 2000, 1877; b) I. P. Beletskaya, A. N. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89; c) R. B. Bedford, C. S. J. Cazin, M. B. Hursthous, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173; d) C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983: e) C. Rocaboy, J. A. Gladysz, New J. Chem. 2003, 27, 39; f) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
22. It has recently been reported that palladium nanoparticles and/or low ligated palladium species are generated in situ from carbopalladacycle complexes to exhibit the extraordinarily high catalytic performance in the Heck reaction; see: a) M. Nowotny, U. Hanefeld, H. van Koningsveld, T. Maschmeyer, Chem. Commun. 2000, 1877; b) I. P. Beletskaya, A. N. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89; c) R. B. Bedford, C. S. J. Cazin, M. B. Hursthous, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173; d) C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983: e) C. Rocaboy, J. A. Gladysz, New J. Chem. 2003, 27, 39; f) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
23. It has recently been reported that palladium nanoparticles and/or low ligated palladium species are generated in situ from carbopalladacycle complexes to exhibit the extraordinarily high catalytic performance in the Heck reaction; see: a) M. Nowotny, U. Hanefeld, H. van Koningsveld, T. Maschmeyer, Chem. Commun. 2000, 1877; b) I. P. Beletskaya, A. N. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89; c) R. B. Bedford, C. S. J. Cazin, M. B. Hursthous, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173; d) C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983: e) C. Rocaboy, J. A. Gladysz, New J. Chem. 2003, 27, 39; f) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
24. It has recently been reported that palladium nanoparticles and/or low ligated palladium species are generated in situ from carbopalladacycle complexes to exhibit the extraordinarily high catalytic performance in the Heck reaction; see: a) M. Nowotny, U. Hanefeld, H. van Koningsveld, T. Maschmeyer, Chem. Commun. 2000, 1877; b) I. P. Beletskaya, A. N. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89; c) R. B. Bedford, C. S. J. Cazin, M. B. Hursthous, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173; d) C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983: e) C. Rocaboy, J. A. Gladysz, New J. Chem. 2003, 27, 39; f) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
25. It has recently been reported that palladium nanoparticles and/or low ligated palladium species are generated in situ from carbopalladacycle complexes to exhibit the extraordinarily high catalytic performance in the Heck reaction; see: a) M. Nowotny, U. Hanefeld, H. van Koningsveld, T. Maschmeyer, Chem. Commun. 2000, 1877; b) I. P. Beletskaya, A. N. Karlstedt, A. V. Mitin, A. V. Cheprakov, G. M. Kazankov, J. Organomet. Chem. 2001, 622, 89; c) R. B. Bedford, C. S. J. Cazin, M. B. Hursthous, M. E. Light, K. J. Pike, S. Wimperis, J. Organomet. Chem. 2001, 633, 173; d) C. S. Consorti, M. L. Zanini, S. Leal, G. Ebeling, J. Dupont, Org. Lett. 2003, 5, 983: e) C. Rocaboy, J. A. Gladysz, New J. Chem. 2003, 27, 39; f) A. H. M. de Vries, J. M. C. A. Mulders, J. H. M. Mommers, H. J. W. Henderickx, J. G. de Vries, Org. Lett. 2003, 5, 3285.
26. M. R. Eberhard, Org. Lett. 2004, 6, 2125.
27. The Heck reaction of 2,3-dihydrofuran with iodobenzene in the presence of the chiral pincer complex 4 gave racemic mixtures of 2-phenyl-2,3-dihydrofuran and 2-phenyl-2,5-dihydrofuran. These observations suggest that the active palladium species generated in situ may not be coordinated with the chiral pyrroloimidazolone groups.
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