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Legros JY, Primault G, Toffano M, et al. Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution. Org Lett. 2000;2(4):433-6doi: 10.1021/ol991274y.
Legros, J. Y., Primault, G., Toffano, M., Riviere, M. A., & Fiaud, J. C. (2000). Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution. Organic letters, 2(4), 433-6. https://doi.org/10.1021/ol991274y
Legros, et al. "Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution." Organic letters vol. 2,4 (2000): 433-6. doi: https://doi.org/10.1021/ol991274y
Legros JY, Primault G, Toffano M, Riviere MA, Fiaud JC. Reactivity of quinoline- and isoquinoline-based heteroaromatic substrates in palladium(0)-catalyzed benzylic nucleophilic substitution. Org Lett. 2000 Feb 24;2(4):433-6. doi: 10.1021/ol991274y. PMID: 10814344.
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Org Lett. 2000 Feb 24;2(4):433-6. doi: 10.1021/ol991274y.

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

Organic letters

Legros, Primault, Toffano, Riviere, Fiaud

Affiliations

  1. Laboratoire de Catalyse Moleculaire associe au C.N.R.S., UPRESA 8075, Institut de Chimie Moleculaire d'Orsay, Universite de Paris-Sud, Orsay, France. [email protected]

PMID: 10814344 DOI: 10.1021/ol991274y

Abstract

[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.

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