Cross-Coupling of N-Heteroaryl Halides with Active Methylene Compounds in the Presence of Tetrakis(triphenylphosphine)palladium

Abstract

The cross-coupling of 3-iodo- and 3-bromopyridine with the carbanions derived from ethyl cyanoacetate and malononitrile in the presence of tetrakis(triphenylphosphine)palladium in 1, 2-dimethoxyethane gave ethyl α-cyanopyridine-3-acetate and 3-pyridinemalononitrile in moderate yields. This palladium-catalyzed cross-coupling proceeded smoothly with halopyrimidines, haloquinolines, haloisoquinolines, and also bromobenzene.