Tsutomu Sakakibara

Alkenylation of 1-acylindoles with olefins bearing electron-withdrawing substituents and palladium acetate

The oxidation of 1-(2,6-dichlorobenzoyl) indole with olefins, such as alkyl acrylates and acrylonitrile, and palladium acetate resulted in selective 3-alkenylation of the indole nucleus. Treatment of 1-acyl-3-methyl-indoles under similar conditions gave the corresponding 2-alkenyl substituted indoles, while the oxidation of 6-oxo-6H-isoindolo[2,1-a]indole gave the corresponding 3-alkenyl substituted indoles.

Formation and reactivity of highly stabilized carbanions and enolates by Pd-catalyzed alkylation of heterocyclic compounds

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