Palladium-Catalyzed cocyclization of arynes with alkynes: Selective synthesis of phenanthrenes and naphthalenes

Journal of the American Chemical Society

Volumn 121, Issue 24, 1999, Pages 5827-5828

  Peña, Diego ^a   Pérez, Dolores ^a   Guitián, Enrique ^a   Castedo, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; NAPHTHALENE DERIVATIVE; PALLADIUM; PHENANTHRENE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0038333050     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9907111     Document Type: Article

References (20)

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4. For general reviews on aryne chemistry, see: (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967. (b) Hart, H. In The Chemistry of Functional Groups, Suppl. C2: The Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1994; pp 1017-1134.
5. For general reviews on aryne chemistry, see: (a) Hoffmann, R. W. Dehydrobenzene and Cycloalkynes; Academic Press: New York, 1967. (b) Hart, H. In The Chemistry of Functional Groups, Suppl. C2: The Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; Wiley: Chichester, 1994; pp 1017-1134.
6. For recent reviews on transition metal complexes of arynes, see: (a) Buchwald, S. L.; Broene, R. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Hegedus, L. H., volume Ed.; Pergamon: Oxford, 1995; Vol. 12, pp 771-784. (b) Bennett, M. A.; Wenger, E. Chem. Ber./Recueil 1997, 130, 1029-1042.
7. For recent reviews on transition metal complexes of arynes, see: (a) Buchwald, S. L.; Broene, R. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Hegedus, L. H., volume Ed.; Pergamon: Oxford, 1995; Vol. 12, pp 771-784. (b) Bennett, M. A.; Wenger, E. Chem. Ber./Recueil 1997, 130, 1029-1042.
8. Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659-2661.
9. Maitlis, P. M. Pure Appl. Chem. 1973, 33, 489-512.
10. Very electron-deficient alkynes (e.g., DMAD) undergo cycloaddition reactions when palladacyclopentadiene complexes are used as precursors of Pd(0) catalysts: (a) Brown, L. D.; Itoh, K.: Suzuki, H.; Hirai, K.; Ibers, J. A. J. Am. Chem. Soc. 1978, 100, 8232-8238. (b) Stephan, C.; Munz, C.; Dieck, H. J. Organomet. Chem. 1993, 452, 223-227.
11. Very electron-deficient alkynes (e.g., DMAD) undergo cycloaddition reactions when palladacyclopentadiene complexes are used as precursors of Pd(0) catalysts: (a) Brown, L. D.; Itoh, K.: Suzuki, H.; Hirai, K.; Ibers, J. A. J. Am. Chem. Soc. 1978, 100, 8232-8238. (b) Stephan, C.; Munz, C.; Dieck, H. J. Organomet. Chem. 1993, 452, 223-227.
12. Cyclization of alkynes by Pd(0) complexes and AcOH occurs via a different mechanism, involving Pd(II)-H complexes as active catalysts: (a) Negishi, E.; Harring, S. L.; Owczarczyk, Z.; Mohamud, M. M.; Ay, A. Tetrahedron Lett. 1992, 33, 3253-3256. (b) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160.
13. Cyclization of alkynes by Pd(0) complexes and AcOH occurs via a different mechanism, involving Pd(II)-H complexes as active catalysts: (a) Negishi, E.; Harring, S. L.; Owczarczyk, Z.; Mohamud, M. M.; Ay, A. Tetrahedron Lett. 1992, 33, 3253-3256. (b) Brown, S.; Clarkson, S.; Grigg, R.; Sridharan, V. Tetrahedron Lett. 1993, 34, 157-160.
14. 4 and electron-deficient alkynes has been described previously: Greaves, E. O.; Lock, C. J. L.; Maitlis, P. M. Can. J. Chem. 1968, 46, 3879-3891.
15. (a) Moseley, K.; Maitlis, P. M. J. Chem. Soc., Chem. Commun. 1971, 1604-1606.
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17. Selective cotrimerization between alkynes of different steric or electronic characters is possible in some cases, but more typically, mixtures of cotrimers and homotrimers are obtained; see, for example, Abdulla, K.; Booth, B. L.; Stacey, C. J. Organomet. Chem. 1985, 293, 103.
18. The formation of a dihydrophenanthrene by reaction of benzyne with a nickelaindane has been described: Cámpora, J.; Llevaría, A.; Moretó, J. M.; Poveda, M. L.; Carmona, E. Organometallics 1993, 12, 4032-4038.
19. This alternative pathway is reminiscent of the mechanism of the Pd-catalyzed annelation of aryl iodides with acetylenes: (a) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946. (b) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536-7537.
20. This alternative pathway is reminiscent of the mechanism of the Pd- catalyzed annelation of aryl iodides with acetylenes: (a) Wu, G.; Rheingold, A. L.; Geib, S. J.; Heck, R. F. Organometallics 1987, 6, 1941-1946. (b) Larock, R. C.; Doty, M. J.; Tian, Q.; Zenner, J. M. J. Org. Chem. 1997, 62, 7536-7537.