Pd(CH3CN)2Cl2-catalyzed oxidative heterodimerization reaction of 2,3-allenamides and 1,2-allenyl ketones: An efficient synthesis of 4-(Furan-3′-yl)-2(5H)-furanimines

Journal of Organic Chemistry

Volumn 70, Issue 16, 2005, Pages 6291-6294

  Ma, Shengming ^a   Gu, Zhenhua ^a   Yu, Zhanqian ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; COMPLEXATION; DIMERIZATION; KETONES; OXIDATION; PALLADIUM COMPOUNDS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

BENZOQUINONE; FURANIMINES; HETERODIMERIZATION; PALLADIUM CATALYSTS;

NITROGEN COMPOUNDS;

2,3 ALLENAMIDE DERIVATIVE; 4 (FURAN 3' YL) 2(5H) FURANIMINE DERIVATIVE; ACETIC ACID; ALLENE DERIVATIVE; AMIDE; BENZOQUINONE; FURAN DERIVATIVE; IMINE; KETONE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CONCENTRATION (PARAMETERS); DIMERIZATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 23044447165     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0507441     Document Type: Article

References (29)

1. (a) The Chemistry of the Allenes; Landor, S. R., Ed.; Academic: London, UK, 1982; Vol. 1.
2. (b) Ma, S. Carbopalladation of Allenes. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; p 1491.
3. (c) Krause, N.; Hashmi, A. S. K., Eds. Modern Allene Chemistry; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
4. (a) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
5. (b) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
6. (c) Ma, S. Acc. Chem. Res. 2003, 36, 701.
7. (d) Hoffmann-Röder, A.; Krause, N. Angew. Chem., Int. Ed. 2004, 43, 1196.
8. (a) Kang, S.; Ha, Y.; Ko, B.; Lim, Y.; Jung, J. Angew. Chem., Int. Ed. 2002, 41, 343.
9. (b) Brummond, K. M.; Chen, H.; Sill, P.; You, L. J. Am. Chem. Soc. 2002, 124, 15186.
10. (c) Trost, B. M.; Jakel, C.; Plietker, B. J. Am. Chem. Soc. 2003, 125, 4438.
11. (d) Franzen, J.; Bäckvall, J.-E. J. Am. Chem. Soc. 2003, 125, 6056.
12. (e) Ohno, H.; Miyamura, K.; Takeoka, Y.; Tanaka, T. Angew. Chem., Int. Ed. 2003, 42, 2647.
13. (f) Huang, J.; Hsung, R. P. J. Am. Chem. Soc. 2005, 127, 50.
14. (g) Chang, K.-J.; Rayabarapu, D. K.; Yang, F.-Y.; Cheng, C.-H. J. Am. Chem. Soc. 2005, 127, 126.
15. (a) Hashmi, A. S. K. Angew. Chem., Int. Ed. Engl. 1995, 34, 1581.
16. (b) Hashmi, A. S. K.; Ruppert, T. L.; Knöfel, T.; Bats, J. W. J. Org. Chem. 1997, 62, 7295.
17. (c) Hashmi, A. S. K.; Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285.
18. (a) Ma, S.; Yu, Z. Org. Lett. 2003, 5, 1507 and 2581.
19. (b) Ma, S.; Yu, Z.; Gu, Z. Chem. Eur. J. 2005, 11, 2351.
20. Ma, S.; Yu, Z. Angew. Chem., Int. Ed. 2002, 41, 1775.
21. (a) Grennberg, H.; Gogoll, A.; Bäckvall, J.-E. Organmetallics 1993, 12, 1790.
22. (b) Albéniz, A. C.; Espinet, P.; Martín-Ruiz, B. Chem. Eur. J. 2001, 7, 2481.
23. (a) Ma, S.; Xie, H. Org. Lett. 2000, 2, 3801.
24. (b) Ma, S.; Xie, H. J. Org. Chem. 2002, 67, 6575.
25. -1. Supplementary crystallographic dada have been deposited at the Cambridge Crystallographic Data Center, CCDC 266567.
26. 000 = 472, final R indices [I > 2σI], R1 = 0.0579, wR = 0.1401; R indices (all data), R1 = 0.0688, wR = 0.1473. Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Center, CCDC 266566.
27. Trieu, N. D.; Elsevier, C. J.; Vrieze, K. J. Organomet. Chem. 1987, 325, C23.
28. Ellis, D. Tetrahedron: Asymmetry 2001, 12, 1589.
29. Constantienx, T.; Buono, G. Org. Synth. 2002, 78, 135.