Novel Highly Regioselective VO(acac)2/TBHP Mediated Oxidation of o-Alkenyl Phenols to o-Hydroxybenzyl Ketones.
2003
A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO(acac)2/TBHP (2 mol %/1.2 equiv) system. VO(acac)2 first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic C−O cleavage and 1,2 hydride migration. The protocol has also been applied to set up a useful and easy one-pot conversion of o-alkenyl phenols to benzo[b]furans by means of the sequential addition of TFA, after the generation of the intermediate o-hydroxybenzyl ketones.
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