Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution
[reaction: see text] Quinolylmethyl, 1-(isoquinolyl)ethyl, and 1-(quinolyl)ethyl acetates reacted with dimethylmalonate anion in the presence of a Pd(0) catalyst to give products of nucleophilic substitution and/or byproducts, depending upon the substitution pattern. The observed side reactions were reduction in the case of primary acetates and elimination or elimination/Michael-type addition sequence for secondary substrates.
Legros
JY
Laboratoire de Catalyse Moleculaire associe au C.N.R.S., UPRESA 8075, Institut de Chimie Moleculaire d'Orsay, Universite de Paris-Sud, Orsay, France. jylegros@icmo.u-psud.fr
Primault
G
Toffano
M
Riviere
MA
Fiaud
JC