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

Autor: 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
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2000 Feb 24; Vol. 2 (4), pp. 433-6.
DOI: 10.1021/ol991274y
Abstrakt: [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.
Databáze: MEDLINE