Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution

Organic Letters

Volumn 2, Issue 4, 2000, Pages 433-436

  Legros, Jean Yves ^a   Primault, Gaëlle ^a   Toffano, Martial ^a   Rivière, Marie Alix ^a   Fiaud, Jean Claude ^a  

^a CNRS   (France)

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Indexed keywords

EID: 0000118679     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991274y     Document Type: Article

References (16)

1. (a) Legros, J. Y.; Fiaud, J. C. Tetrahedron Lett. 1992, 33, 2509-2510.
2. (b) Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron 1995, 51, 3235-3246.
3. (c) Legros, J. Y.; Toffano, M.; Fiaud, J. C. Tetrahedron: Asymmetry 1995, 6, 1899-1902.
4. Toffano, M.; Legros, J. Y.; Fiaud, J. C. Tetrahedron Lett. 1997, 38, 77-80.
5. (a) Boutros, A.; Legros, J. Y., Fiaud, J. C. Tetrahedron Lett. 1999, 40, 7329-7332.
6. (b) Boutros, A.; Legros, J. Y., Fiaud, J. C. Tetrahedron, accepted for publication.
7. Legros, J. Y., Primault, G., Fiaud, J. C., unpublished work.
8. Taylor, R. J. Chem. Soc. B 1971, 2382-2387.
9. Clyde, E., Taylor, R. J. Chem. Soc., Perkin Trans. 2 1975, 1783-1791.
10. All new compounds were characterized by proton and carbon-13 NMR, IR, and either HRMS or elemental analysis.
11. 7; no reduction product was detected in these conditions.
12. (a) Oda, R.; Teramura, K.; Tanimoto, S.; Nomura, M.; Suda, H.; Matsuda, K. Bull. Inst. Chem. Res. Kyoto Univ. 1955, 33, 117-125.
13. (b) Boekelheide, V.; Sieg, A. L. J. Org. Chem. 1954, 19, 587-592.
14. Compound 10a was already prepared by a Stille reaction on 2-quinolyl triflate: Crisp, G. T.; Papadopoulos, S. Aust. J. Chem. 1989, 42, 279-285.
15. 1-palladium intermediate analogous to 14b; because of the electron-withdrawing properties of the pyridinic nitrogen atom, the aromatic C=C double bond is very likely to be weakly interacting with palladium. We thank one of the referees for this suggestion.
16. 4) and concentrated. The crude product was purified by flash chromatography (silica, heptane/ethyl acetate 70:30) to give dimethyl 2-(1-(4-quinolyl(ethyl)propanedioate 8c (212 mg, 0.74 mmol, 74%).