Palladium-assisted N-alkylation of indoles: attempted application to polycyclization

…, PM Winton, S Varaprath

Index: Hegedus, Louis S.; Winton, Peter M.; Varaprath Sudarsanan Journal of Organic Chemistry, 1981 , vol. 46, # 11 p. 2215 - 2221

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Citation Number: 46

Abstract

The palladium (I1) complexes of the olefins ethene, propene, and 1-hexene reacted with 1- lithioindole to produce N-alkylated indoles exclusively. Attempts to perform this N-alkylation intramolecularly (to form tricyclic material from 2-allylskatole) failed. Anilines with dienic side chains in the 2-position were subjected to Pd (I1)-assisted cyclization conditions in attempts to induce polycyclization. However, only monocyclization was observed.