Bu₄NI-Catalyzed C–C Bond Cleavage and Oxidative Esterification of Allyl Alcohols with Toluene Derivatives

^§ These authors contributed equally to this work.

Abstract

A novel oxidative esterification of 1-arylprop-2-en-1-ols with toluene derivatives catalyzed by tetrabutylammonium iodide (TBAI) is reported. The optimization of the reaction conditions illustrates that each of experiment parameters including the catalyst, solvent, and oxidant is significant for present oxidative functionalization. This metal-free protocol has a broad substrate scope including the halogen groups for further functionalization and enriches the reactivity profile of allyl alcohol and toluene derivatives. In addition, this protocol represents a new transformation of allyl alcohol involving C–C bond cleavage and C–O bond forming.

Key words

esterification - allyl alcohol - toluene derivative - oxidative coupling - C–H activation

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