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Site-selective electrooxidation of methylarenes to aromatic acetals.
- Source :
-
Nature communications [Nat Commun] 2020 Jun 01; Vol. 11 (1), pp. 2706. Date of Electronic Publication: 2020 Jun 01. - Publication Year :
- 2020
-
Abstract
- Aldehyde is one of most synthetically versatile functional groups and can participate in numerous chemical transformations. While a variety of simple aromatic aldehydes are commercially available, those with a more complex substitution pattern are often difficult to obtain. Benzylic oxygenation of methylarenes is a highly attractive method for aldehyde synthesis as the starting materials are easy to obtain and handle. However, regioselective oxidation of functionalized methylarenes, especially those that contain heterocyclic moieties, to aromatic aldehydes remains a significant challenge. Here we show an efficient electrochemical method that achieves site-selective electrooxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition-metal catalysts. The acetals can be converted to the corresponding aldehydes through hydrolysis in one-pot or in a separate step. The synthetic utility of our method is highlighted by its application to the efficient preparation of the antihypertensive drug telmisartan.
- Subjects :
- Acetals chemical synthesis
Aldehydes chemical synthesis
Amidines chemistry
Benzimidazoles chemistry
Catalysis
Hydrocarbons, Aromatic chemical synthesis
Hydrolysis
Molecular Structure
Oxidants chemistry
Oxidation-Reduction
Acetals chemistry
Aldehydes chemistry
Electrochemical Techniques methods
Hydrocarbons, Aromatic chemistry
Models, Chemical
Subjects
Details
- Language :
- English
- ISSN :
- 2041-1723
- Volume :
- 11
- Issue :
- 1
- Database :
- MEDLINE
- Journal :
- Nature communications
- Publication Type :
- Academic Journal
- Accession number :
- 32483217
- Full Text :
- https://doi.org/10.1038/s41467-020-16519-8