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

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...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2010-08, Vol.66 (34), p.6919-6923
Main Authors: Dai, Shiyao, Wu, Jinchuan, Wang, Zunsheng, Chen, Yongzheng, Li, Zhi
Format: Article
Language:English
Subjects:
Alkyl toluenes
Benzyl alcohols
Bioconversions. Hemisynthesis
Biological and medical sciences
Biotechnology
Biotransformations
Chemistry
Enzyme catalysis
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
Hydroxylations
Methods. Procedures. Technologies
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.06.039