HETEROCYCLES

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■ Formation and Reactivity of Highly Stabilized Carbanions and Enolates by Pd-Catalyzed Alkylation of Heterocyclic Compounds

Tsutomu Sakakibara,* Takashi Kume, Kumiko Shimohara, Hiroshi Fujishima, Shunpei Hara, and Toshifumi Shimoda

*Institute of Chemistry, College of Liberal Arts, Kagoshima University, 1-21-35 Korimoto, Kagoshima 890-0065, Japan

Abstract

Highly stabilized carbanion and enolate salts, heterocycle-substituted sodiomalononitrile and sodiocyanoacetates, were synthesized via Pd-catalyzed ring-alkylation of bromoheterocyclic compounds and shown to be useful intermediates for the synthesis of various alkyl-substituted heterocyclic compounds.