O-Quinone methide with overcrowded olefinic core as a catalytically-active surrogate of triarylmethylium salt for dehydridative oxidation of benzylic alcohols under aerobic photoirradiation conditions

Abstract

An o-quinone methide (o-QM) competent as a catalyst for the dehydridative oxidation of benzylic alcohols was developed. The introduction of an overcrowded olefinic component into the o-QM induced structural distortion, beneficial for imparting triarylmethylium character and regenerability. The zwitterionc resonance form of the o-QM, generated via photoexcitation and subsequent relaxation, exerted the dehydridation activity. Density functional theory calculations were conducted to gain insights into the operative catalytic process.