Tetrabutylammonium Pyridin-2-olate: A New Reagent for the Efficient Synthesis of N-Aryl Pyridin-2-ones

Abstract

A new reagent, tetrabutylammonium pyridin-2-olate, was prepared and its application to the efficient synthesis of N-aryl pyridine-2-ones was demonstrated using CuI-catalyzed coupling reactions with aryl iodides. This coupling reaction is mild, high-yielding, and remarkably chemoselective (N- vs. O-arylation). It is also compatible with substrates containing labile functional groups.

Key words

preparation - tetrabutylammonium pyridin-2-olate - aryl iodides - CuI-catalyzed coupling reaction - N-aryl pyridin-2-ones

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17

A similar low yield (22%) was reported by Filipski and coworkers for the copper-catalyzed coupling reaction of pyridin-2(1H)-one with methyl 4-iodobenzoate, see ref 12e.