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New Protocols for the Synthesis of Condensed Heterocyclic Rings Through Palladium-Catalyzed Aryl Coupling Reactions

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Abstract

In the process of developing our aryl coupling methodology according to which aryl iodides are caused to react with aryl bromides under the catalytic action of a dual palladium/norbornene catalyst, we have worked out new protocols to cause appropriate functional groups in the aryl halides to form heterocyclic rings condensed with the first-formed biaryl intermediate. Carbazoles, dibenzopyrans, phenanthridines and azaphenanthrenes have been obtained with good yields in one-pot reactions under mild conditions.

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References

  1. Catellani M, Motti E, Della Ca’ N (2008) Acc Chem Res 41:1512

    Article  CAS  Google Scholar 

  2. Catellani M, Motti E, Deledda S, Faccini F (2005) In: Sowa JR Jr (ed) Catalysis of organic reactions. Taylor and Francis, New York, pp 449–458

    Google Scholar 

  3. Faccini F, Motti E, Catellani M (2004) J Am Chem Soc 126:78

    Article  CAS  Google Scholar 

  4. Ferraccioli R, Carenzi D, Rombolà O, Catellani M (2004) Org Lett 6:4759

    Article  CAS  Google Scholar 

  5. Mariampillai B, Alliot J, Li M, Lautens M (2007) J Am Chem Soc 129:15372

    Article  CAS  Google Scholar 

  6. Della Ca’ N, Sassi G, Catellani M (2008) Adv Synth Catal 350:2179

    Article  Google Scholar 

  7. Motti E, Faccini F, Ferrari I, Catellani M, Ferraccioli R (2006) Org Lett 8:3967

    Article  CAS  Google Scholar 

  8. Della Ca’ N, Motti E, Catellani M (2008) Adv Synth Catal 350:2513

    Article  Google Scholar 

  9. Della Ca’ N, Motti E, Mega A, Catellani M (in press) Adv Synth Catal

  10. Cordell GA (ed) (2008) The alkaloids, vol 65. Academic Press, Amsterdam

    Google Scholar 

  11. Katritzky AR, Rees CW, Scriven EF (eds) (1996) Comprehensive heterocyclic chemistry II. Pergamon, Oxford

    Google Scholar 

  12. Naid T, Kitahara T, Kaneda M, Nakamura S (1987) J Antibiot 40:157

    CAS  Google Scholar 

  13. Horino H, Arai M, Inoue N (1974) Tetrahedron Lett 647

  14. Li C-S, Cheng C-H, Liao F-L, Wang S-L (1991) Chem Commun 710

  15. Portnoy M, Ben-David Y, Rousso I, Milstein D (1994) Organometallics 13:3465

    Article  CAS  Google Scholar 

  16. Catellani M, Mealli C, Motti E, Paoli P, Perez-Carreno E, Pregosin PS (2002) J Am Chem Soc 124:4336

    Article  CAS  Google Scholar 

  17. Beletskaya IP, Cheprakov AV (2004) J Organomet Chem 689:4055

    Article  CAS  Google Scholar 

  18. Catellani M, Chiusoli GP (1992) J Organomet Chem 425:151

    Article  CAS  Google Scholar 

  19. Catellani M, Chiusoli GP (1988) J Organomet Chem 346:C27

    Article  CAS  Google Scholar 

  20. Liu C-H, Li C-S, Cheng C-H (1994) Organometallics 13:18

    Article  CAS  Google Scholar 

  21. Dyker G (1999) Angew Chem Int Ed 38:1699

    Article  CAS  Google Scholar 

  22. Kakiuchi F, Chatani N (2003) Adv Synth Catal 345:1077

    Article  CAS  Google Scholar 

  23. Campeau L-C, Fagnou K (2006) Chem Commun 1253

  24. Alberico D, Scott ME, Lautens M (2007) Chem Rev 107:174

    Article  CAS  Google Scholar 

  25. Larock RC (2005) In: Sowa JR Jr (ed) Catalysis of organic reactions. Taylor and Francis, New York, pp 435–447

    Google Scholar 

  26. Zeni G, Larock RC (2006) Chem Rev 106:4644

    Article  CAS  Google Scholar 

  27. Candito DA, Lautens M (2009) Angew Chem Int Ed 48:6713

    Article  CAS  Google Scholar 

  28. Ackerman L (2009) Modern Arylation Methods. Wiley-VCH, Weinheim See for reviews

    Book  Google Scholar 

  29. Negishi E-I (ed) (2002) Handbook of organopalladium chemistry for organic synthesis. Wiley-Interscience, New York

    Google Scholar 

  30. Cárdenas DJ, Martín-Matute B, Echavarren AM (2006) J Am Chem Soc 128:5033

    Article  Google Scholar 

  31. Mota AJ, Dedieu A (2006) Organometallics 25:3130

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support from MIUR and the University of Parma is gratefully acknowledged.

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Correspondence to Marta Catellani.

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Catellani, M., Motti, E. & Della Ca’, N. New Protocols for the Synthesis of Condensed Heterocyclic Rings Through Palladium-Catalyzed Aryl Coupling Reactions. Top Catal 53, 991–996 (2010). https://doi.org/10.1007/s11244-010-9548-y

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  • DOI: https://doi.org/10.1007/s11244-010-9548-y

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