Facile palladium-mediated substitution of chlorine in 2-chloroquinolines

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8281-8284

  Ciufolini, Marco A ^a   Mitchell, James W ^a   Roschangar, Frank ^a,b  

^a RICE UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS;

LATEOLABRAX JAPONICUS;

EID: 0030580372     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01937-5     Document Type: Article

References (17)

1. 3. Heck, R. F. Org. React. 1989, 27, 345.
2. 4. The term "Castro-Stephens reaction," as used herein, actually refers to the Linstrumelle modification (Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1985, 26, 3811) of the Sonogashira protocol (Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467) for the original Castro-Stephens reaction (Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313).
3. 4. The term "Castro-Stephens reaction," as used herein, actually refers to the Linstrumelle modification (Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1985, 26, 3811) of the Sonogashira protocol (Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467) for the original Castro-Stephens reaction (Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313).
4. 4. The term "Castro-Stephens reaction," as used herein, actually refers to the Linstrumelle modification (Guillerm, D.; Linstrumelle, G. Tetrahedron Lett. 1985, 26, 3811) of the Sonogashira protocol (Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467) for the original Castro-Stephens reaction (Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313).
5. 5. Cf., e.g., Stille, J. K.; Groh, B. L. J. Am. Chem. Soc. 1987, 109, 813.
6. 6. Suzuki, A.; Miyaura, N. J. Soc. Synth. Org. Chem. Jpn. 1993, 77, 91.
7. 7. Ben-David, Y.; Portnoy, M.; Milstein, D. J. Am. Chem. Soc. 1989, 111, 8742.
8. 8. Meth-Cohn, O.; Narine, B.; Tarnowski, B. J. Chem. Soc., Perkin Trans. I 1981, 1520; 1537.
9. 9. Rocca, P.; Marsais, F.; Godard, A.; Quéguiner, G. Tetrahedron Lett. 1993, 34, 2937.
10. 10. Cheng, C.-C.; Yan, S.-J. Org. React. 1982, 23, 37.
11. 11. For an excellent review of Ni- and Pd-catalyzed reactions of heterocyclic systems see: Kalinin, V. N. Synthesis 1992, 413.
12. 12. Freshly prepared according to Coulson, D. R. Inorg. Synth. 1977, 13, 121.
13. 2O (1 eq.) with good stirring, followed by filtration of the white ppt., washing with ether and vacuum drying.
14. 14. Watanabe, T.; Miyaura, N.; Suzuki, A. Synlett 1992, 207.
15. 15. Ciufolini, M. A.; Qi, H. B.; Browne, M. E. J. Org. Chem. 1988, 53, 4149
16. 16. Frank, W. C.; Kim, Y. C.; Heck, R. F. J. Org. Chem. 1978, 43, 2947. See also ref. 3.
17. 3: 231.0895 (M+), found: 201.0895.