Copper-catalyzed selective arylations of benzoxazoles with aryl iodides

The Journal of Organic Chemistry
Donghae KimMin Kim

Abstract

A copper-catalyzed direct ring-opening double N-arylation of benzoxazoles with aryl iodides has been developed. The present system exhibits high selectivity despite competition from C-arylation. The selectivity between ring-opening N-arylation and C-arylation was controlled by the choice of reaction vessel. The nitrile bound bis(triphenylphosphine)copper cyanide was identified as the active catalytic species for both reactions, and when combined with a nitrile-containing solvent, enhanced the reaction efficiency.

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Citations

Aug 20, 2015·Organic & Biomolecular Chemistry·Rafał Loska, Patrycja Bukowska
Dec 15, 2016·The Journal of Organic Chemistry·Chao GaoHuayue Wu
Dec 17, 2016·The Journal of Organic Chemistry·Roy P LesterJason E Camp

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