TBAI-catalyzed oxidative cross-coupling of phenols and 2-aminoacetophenones

Organic Letters
Wei Xu, Boris J Nachtsheim

Abstract

An iodide-catalyzed oxidative cross-coupling between phenols and 2-aminoacetophenones has been developed. Using catalytic amounts of tetrabutylammoniumiodide (TBAI) as an iodine-containing catalyst and aqueous solutions of tert-butyl hydro-peroxide (TBHP) as the stoichiometric co-oxidant, a variety of α-phenoxylated 2-aminoacetophenones could be obtained in yields of up to 92% after remarkably short reaction times (20 min). This is a very rare example for an iodide-catalyzed intermolecular cross-coupling utilizing phenols. However, this efficient methodology could be further extended toward an intramolecular variant which gives direct access to a range of dihydro-4H-benzo[e][1,3]oxazin-4-ones.

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Citations

Sep 3, 2016·Organic Letters·Rongwei Jin, Frederic W Patureau
Jul 4, 2017·Chemical Communications : Chem Comm·Zhao-Ying YangBin Wang
May 17, 2018·Chemistry : a European Journal·Monalisa GoswamiFrederic W Patureau

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