Highly chemo- and regio-selective hydroxylations of o- and m-substituted toluenes to benzyl alcohols with Cellulosimicrobium cellulans EB-8-4

Abstract

Highly chemo- and regio-selective benzylic hydroxylations of o- and m-substituted toluenes were achieved with the easily available and easy-to-handle resting cells of Cellulosimicrobium cellulans EB-8-4 as biocatalysts, giving the corresponding benzyl alcohols as single product. Benzyl alcohols were obtained in 78–94% yield, demonstrating the first green, clean, and simple method for the preparation of benzyl alcohols via hydroxylations. Biotransformation of 4-methylbenzyl chloride with the same strain gave 4-methylbenzyl alcohol in 67–81% yield, suggesting a novel dehalogenation activity of the cells and providing a novel, green, and efficient method for the preparation of 4-methylbenzyl alcohol as well as the application potential in biodegradation of chlorine-containing aromatics.