Tetrahedron

Homolytic alkylation of heteroaromatic bases: The problem of monoalkylation

F Fontana, F Minisci, MCN Barbosa, E Vismara

Index: Fontana; Minisci; Barbosa, M. C. Nogueira; Vismara Tetrahedron, 1990 , vol. 46, # 7 p. 2525 - 2538

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Citation Number: 30

Abstract

The silver-catalyzed decarboxylation of carboxylic acids by persulphate leads to alkyl radicals, which have been utilized for the selective alkylation of heteroaromatic bases. The method is particularly efficient in a water-chlorobenzene two-phase system for two reasons: it considerably increases the selectivity in monoalkylation when more positions of high nucleophilic reactivity (ie α and γ) are available in the heterocyclic ring (ie quinoline, 4- ...