Solid phase palladium-catalysed C-C bond formation in the pyridine series: Access to aryl and alkynyl pyridylpiperazines

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5613-5616

  Louërat, Frédéric ^a   Gros, Philippe ^a   Fort, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNYL GROUP; PALLADIUM; PIPERAZINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BOND; DIMERIZATION; REACTION ANALYSIS; SOLID; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE;

LATEOLABRAX JAPONICUS;

EID: 0037829773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01370-4     Document Type: Article

References (24)

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5. For reviews, see: (a) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555; (b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202; (c) Reginato, G.; Taddei, M. Farmaco, 2002, 57, 373-384; (d) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885-939.
6. For reviews, see: (a) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555; (b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202; (c) Reginato, G.; Taddei, M. Farmaco, 2002, 57, 373-384; (d) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885-939.
7. For reviews, see: (a) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497-555; (b) Sammelson, R. E.; Kurth, M. J. Chem. Rev. 2001, 101, 137-202; (c) Reginato, G.; Taddei, M. Farmaco, 2002, 57, 373-384; (d) Bräse, S.; Kirchhoff, J. H.; Köbberling, J. Tetrahedron 2003, 59, 885-939.
8. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
9. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
10. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
11. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
12. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
13. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
14. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
15. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
16. For Suzuki couplings see, for example: (a) Wenderborn, S.; Berteina, S.; Brill, K.-D.; De Mesmaeker, A. Synlett 1998, 671-675; (b) Chamoin, S.; Houldsworth, S.; Kruse, C. G.; Bakker, W. I.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4179-4182; (c) Li, W.; Burgess, K. Tetrahedron Lett. 1999, 40, 6527-6530. For Stille reactions see (d) Desphande, M. S. Tetrahedron Lett. 1994, 35, 5613-5614; (e) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306-3307; (f) Chamoin, S.; Houldsworth, S.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4175-4178. For Sonogashira couplings see: (g) Young, J. K.; Nelson, J. C.; Moore, J. C. J. Am. Chem. Soc. 1994, 116, 10841-10842; (h) Jones, L.; Schumm, J. S.; Tour, J. M. J. Org. Chem. 1997, 62, 1388-1410; (i) Dyatkin, A. B.; Rivero, R. A. Tetrahedron Lett. 1998, 39, 3647-3650.
17. Lago M.A., Nguyen T.T., Bhatnagar P. Tetrahedron Lett. 39:1998;3885-3888.
18. For a review on this reaction in solution phase see Gros, Ph.; Fort, Y. Eur. J. Org. Chem. 2002, 20, 3375-3383.
19. Gros Ph., Louërat F., Fort Y. Org. Lett. 4:2002;1759-1761.
20. 3): δ 171.8, 158.7, 156.1, 135.1, 123.2, 105.7, 52.7, 45.0, 43.6, 29.2, 27.9, 26.9, 13.8. Resin 2 was prepared identically to 3 except that a solution of zinc bromide (4.1 g, 18 mmoles) in THF (20 mL) was used.
21. 2O, THF and ether. Usual cleavage and chromatography afforded 4a (230 mg, 40%).
22. Homocoupling was demonstrated by isolation of a large amount of 2,2′-bipyridine in the filtrate.
23. 3): δ 158.7, 156.0, 153.6, 138.2, 137.0, 131.9, 128.7, 128.5, 128.0, 127.1, 113.1, 106.2, 52.8, 45.0, 43.6.
24. +), 316 (34), 315 (30), 229 (14), 215 (22), 202 (100), 58 (7).