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

Authors
Legros, JY Primault, G Toffano, M Riviere, MA Fiaud, JC
Citation
Jy. Legros et al., Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution, ORG LETT, 2(4), 2000, pp. 433-436
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
4
Year of publication
2000
Pages
433 - 436
Database
ISI
SICI code
1523-7060(20000224)2:4<433:ROQAIH>2.0.ZU;2-W
Abstract
[GRAPHICS] Quinolylmethyl, 1-(isoquinolyl)ethyl, and 1-(quinolyl)ethyl acetates reacte d with dimethylmalonate anion in the presence of a Pd(0) catalyst to give p roducts of nucleophilic substitution and/or byproducts, depending upon the substitution pattern, The observed side reactions were reduction in the cas e of primary acetates and elimination or elimination/Michael-type addition sequence for secondary substrates.