Palladium-catalyzed carbonylative annulation of terminal alkynes: Synthesis of coumarins and 2-quinolones

Journal of Organometallic Chemistry

Volumn 687, Issue 2, 2003, Pages 425-435

  Kadnikov, Dmitry V ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Annulation; Carbon monoxide; Palladium; Terminal alkyne

Indexed keywords

ALKYL GROUP; ALKYNE DERIVATIVE; ANILINE DERIVATIVE; CARBON; CARBON MONOXIDE; CHROMONE DERIVATIVE; COUMARIN DERIVATIVE; ESTER DERIVATIVE; FUNCTIONAL GROUP; HYDROXYL GROUP; NITRILE; PALLADIUM; PHENOL DERIVATIVE; PYRIDINE; QUINOLONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CONTROLLED STUDY; EXPERIMENTATION; ISOTOPE LABELING; PHASE TRANSITION; REACTION ANALYSIS; SYNTHESIS;

EID: 0344875107     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(03)00786-1     Document Type: Article

References (31)

1. Tsuji J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis 1995 John Wiley & Sons, Ltd Chichester
2. Schore N.E. Chem. Rev. 88 1988 1081
3. Cacchi S. J. Organomet. Chem. 576 1999 42
4. Larock R.C. J. Organomet. Chem. 576 1999 111
5. Larock R.C. Pure Appl. Chem. 71 1999 1435
6. Arcadi A. Marinelli F. Cacchi S. Synthesis 1986 749
7. Sakamoto T. Kondo Y. Yamanaka H. Heterocyles 24 1986 31
8. Yasuhara A. Kanamori Y. Kaneko M. Numata A. Kondo Y. Sakamoto T. J. Chem. Soc., Perkin Trans. 1 1999 529
9. Liao H.-Y. Cheng C.-H. J. Org. Chem. 60 1995 3711
10. Roesch K.R. Larock R.C. J. Org. Chem. 67 2002 86
11. Zhang H. Larock R.C. Tetrahedron Lett. 43 2002 1359
12. Sonogashira K. in: Diederich F. Stang P.J. (Eds.), Metal-catalyzed Cross-coupling Reactions 1998 203 Wiley-VCH Weinheim
13. Kadnikov D.V. Larock R.C. Org. Lett. 2 2000 3643
14. D.V. Kadnikov, R.C. Larock, manuscript in preparation.
15. An Z.-W. Catellani M. Chiusoli G.P. Gazz. Chim. Ital. 120 1990 383
16. An Z.-W. Catellani M. Chiusoli G.P. J. Organomet. Chem. 371 1989 C51
17. Ciattini P.G. Morera E. Ortar G. Rossi S.S. Tetrahedron 47 1991 9449
18. Kalinin V.N. Shostakovsky M.V. Ponomaryov A.B. Tetrahedron Lett. 31 1990 4073
19. Torii S. Okumoto H. Xu L.H. Sadakane M. Shostakovsky M.V. Ponomaryov A.B. Kalinin V.N. Tetrahedron 49 1993 9773
20. Miao H. Yang Z. Org. Lett. 2 2000 1765
21. Torii S. Okumoto H. Xu L.H. Tetrahedron Lett. 32 1991 237
22. Trost B.M. Sorum M.T. Chan C. Harms A.E. Rühter G. J. Am. Chem. Soc. 119 1997 698
23. Negishi E. Ay M. Sugihara T. Tetrahedron 49 1993 5471
24. Bae J.W. Lee S.H. Cho Y.J. Jung Y.J. Hwang H.-J. Yoon C.M. Tetrahedron Lett. 41 2000 5899
25. Dang H. Garcia-Garibay M.A. J. Am. Chem. Soc. 123 2001 355
26. Rossi E. Arcadi A. Abbiati G. Attanasi O.A. Crescentini L.D. Angew. Chem. Int. Ed. 41 2002 1400
27. Kondo Y. Kojima S. Sakamoto T. J. Org. Chem. 62 1997 6507
28. Yoneda E. Sugioka T. Hirao K. Zhang S.-W. Takahashi S. J. Chem. Soc., Perkin Trans. 1 1998 477
29. Bouvier P. Andrieux J. Cunha H. Molho D. Bull. Soc. Chim. Fr. 1977 1187
30. Alberosa A. Calvo B. Ortega A.G. Pedrosa R. J. Chem. Soc., Perkin Trans. 1 1992 3075
31. Terpko M.O. Heck R.F. J. Am. Chem. Soc. 101 1979 5281