Solid acid-catalysed michael-type conjugate addition of indoles to electron-poor C=C bonds: Towards high atom economical semicontinuous processes

Advanced Synthesis and Catalysis

Volumn 346, Issue 5, 2004, Pages 545-548

  Bandini, Marco ^a   Fagioli, Matteo ^a   Umani Ronchi, Achille ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

Amberlyst 15; Continuous process; Friedel Crafts alkylation; Heterogeneous catalysis; Indoles; Michael addition

Indexed keywords

ACID; CARBON; INDOLE DERIVATIVE; KETONE DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; ATOM; CATALYSIS; CATALYST; CONJUGATION; ELECTRON; FRIEDEL CRAFTS REACTION; MICHAEL ADDITION; SOLID;

EID: 2542504322     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200303213     Document Type: Article

References (28)

1. a) K. Wilson, J. H. Clark, Pure Appl. Chem. 2000, 72, 1313-1319;
2. b) T. Okuhara, Chem. Rev. 2002, 102, 3641-3666;
3. c) J. H. Clark, Acc. Chem. Res. 2002, 35, 791-797.
4. P. Espeel, R. Parton, H. Toufar, J. Martens, W. Hölderich, P. Jacobs, Zeolite Effects in Organic Catalysis, In: A. Vaccari, Applied Clay Science 1999, 14, 161-198.
5. K. Tanabe, W. F. Hölderich, Appl. Catal. A: Gen. 1999, 181, 399-434.
6. a) M. Bandini, M. Fagioli, P. Melchiorre, M. Melloni, A. Umani-Ronchi, Tetrahedron Lett. 2003, 44, 5843-5846;
7. b) D. A. Evans, K. A. Scheidt, K. R. Fandrick, H. Wai Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780-10781;
8. c) M. Bandini, A. Melloni, S. Tommasi, A. Umani-Ronchi, Helv. Chim. Acta 2003, 86, 3753-3763;
9. d) M. Bandini, M. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556, and references cited therein.
10. d) M. Bandini, M. Melloni, A. Umani-Ronchi, Angew. Chem. 2004, 116, 560-566; Angew. Chem. Int. Ed. 2004, 43, 550-556, and references cited therein.
11. a) M. Bandini, P. Melchiorre, A. Melloni, A. Umani-Ronchi, Synthesis 2002, 1110-1114;
12. b) M. Bandini, P. G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, A. Umani-Ronchi, J. Org. Chem. 2002, 67, 3700-3704;
13. c) M. Bandini, M. Fagioli, A. Melloni, A. Umani-Ronchi, Synthesis 2003, 397-402;
14. d) M. Agnusdei, M. Bandini, A. Melloni, A. Umani-Ronchi, J. Org. Chem. 2003, 68, 7126-7129.
15. Although extensive efforts have been devoted to the heterogenously catalysed synthesis of bis- and tris(indolyl)-methanes, see: M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002, 43, 4075-4078; C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557-559; G. Panieres-Carrillo, J. G. García-Estrada, J. L. Gutíerrez-Ramírez, C. Alvarez-Toledano, Green. Chem. 2003, 5, 337-339, only few examples of solid acids promoted 1,4-additions were reported, see: M. Chakrabarty, R. Basak, N. Ghosh, Tetrahedron Lett. 2001, 42, 3913-3915; G. Bartoli; M. Bartolacci; M. Bosco; G. Foglia; A. Giuliani; E. Marcantoni; L. Sambri; E. Torregiani; J. Org. Chem. 2003, 68, 4594-4597.
16. Although extensive efforts have been devoted to the heterogenously catalysed synthesis of bis- and tris(indolyl)-methanes, see: M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002, 43, 4075-4078; C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557-559; G. Panieres-Carrillo, J. G. García-Estrada, J. L. Gutíerrez-Ramírez, C. Alvarez-Toledano, Green. Chem. 2003, 5, 337-339, only few examples of solid acids promoted 1,4-additions were reported, see: M. Chakrabarty, R. Basak, N. Ghosh, Tetrahedron Lett. 2001, 42, 3913-3915; G. Bartoli; M. Bartolacci; M. Bosco; G. Foglia; A. Giuliani; E. Marcantoni; L. Sambri; E. Torregiani; J. Org. Chem. 2003, 68, 4594-4597.
17. Although extensive efforts have been devoted to the heterogenously catalysed synthesis of bis- and tris(indolyl)-methanes, see: M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002, 43, 4075-4078; C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557-559; G. Panieres-Carrillo, J. G. García-Estrada, J. L. Gutíerrez-Ramírez, C. Alvarez-Toledano, Green. Chem. 2003, 5, 337-339, only few examples of solid acids promoted 1,4-additions were reported, see: M. Chakrabarty, R. Basak, N. Ghosh, Tetrahedron Lett. 2001, 42, 3913-3915; G. Bartoli; M. Bartolacci; M. Bosco; G. Foglia; A. Giuliani; E. Marcantoni; L. Sambri; E. Torregiani; J. Org. Chem. 2003, 68, 4594-4597.
18. Although extensive efforts have been devoted to the heterogenously catalysed synthesis of bis- and tris(indolyl)-methanes, see: M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002, 43, 4075-4078; C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557-559; G. Panieres-Carrillo, J. G. García-Estrada, J. L. Gutíerrez-Ramírez, C. Alvarez-Toledano, Green. Chem. 2003, 5, 337-339, only few examples of solid acids promoted 1,4-additions were reported, see: M. Chakrabarty, R. Basak, N. Ghosh, Tetrahedron Lett. 2001, 42, 3913-3915; G. Bartoli; M. Bartolacci; M. Bosco; G. Foglia; A. Giuliani; E. Marcantoni; L. Sambri; E. Torregiani; J. Org. Chem. 2003, 68, 4594-4597.
19. Although extensive efforts have been devoted to the heterogenously catalysed synthesis of bis- and tris(indolyl)-methanes, see: M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 2002, 43, 4075-4078; C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 2003, 345, 557-559; G. Panieres-Carrillo, J. G. García-Estrada, J. L. Gutíerrez-Ramírez, C. Alvarez-Toledano, Green. Chem. 2003, 5, 337-339, only few examples of solid acids promoted 1,4-additions were reported, see: M. Chakrabarty, R. Basak, N. Ghosh, Tetrahedron Lett. 2001, 42, 3913-3915; G. Bartoli; M. Bartolacci; M. Bosco; G. Foglia; A. Giuliani; E. Marcantoni; L. Sambri; E. Torregiani; J. Org. Chem. 2003, 68, 4594-4597.
20. Good yields were also obtained in the addition of different indoles to 2: 1-methylindole (80%), 1,2-dimethylindole (55%).
21. Reaction times to complete conversion: I cycle 18 h, II cycle 22 h, III cycle 26 h, IV cycle 28 h, V cycle 30 h.
22. Recent examples of continuous solid acid-catalysed reactions, see [hydrogenation]: M. G. Hitzler, M. Poliakoff, Chem. Commun. 1997, 1667-1668; [FC]: M. G. Hitzler, F. R. Smail, S. K. Ross, M. Poliakoff, Chem. Commun. 1998, 359-360; [dehydration of alcohols]: W. K. Gray, F. R. Smail, M. G. Hitzler, S. K. Ross, M. Poliakoff, J. Am. Chem. Soc. 1999, 121, 10711-10718.
23. Recent examples of continuous solid acid-catalysed reactions, see [hydrogenation]: M. G. Hitzler, M. Poliakoff, Chem. Commun. 1997, 1667-1668; [FC]: M. G. Hitzler, F. R. Smail, S. K. Ross, M. Poliakoff, Chem. Commun. 1998, 359-360; [dehydration of alcohols]: W. K. Gray, F. R. Smail, M. G. Hitzler, S. K. Ross, M. Poliakoff, J. Am. Chem. Soc. 1999, 121, 10711-10718.
24. Recent examples of continuous solid acid-catalysed reactions, see [hydrogenation]: M. G. Hitzler, M. Poliakoff, Chem. Commun. 1997, 1667-1668; [FC]: M. G. Hitzler, F. R. Smail, S. K. Ross, M. Poliakoff, Chem. Commun. 1998, 359-360; [dehydration of alcohols]: W. K. Gray, F. R. Smail, M. G. Hitzler, S. K. Ross, M. Poliakoff, J. Am. Chem. Soc. 1999, 121, 10711-10718.
25. a) P. Tundo, Continuous Flow Methods in Organic Synthesis, Prentice Hall PTR: Upper Side River, New York, 1992;
26. b) N. G. Anderson, Org. Process Res. Dev. 2001, 5, 613-621.
27. Mass flow rate of reactant for mass of catalyst utilised in the reactor.
28. For an elegant study on the environmental assessment of organic reactions, see: M. Eissen, J. O. Metzger, Chem. Eur. J. 2002, 8, 3580-3585.