Site-selective electrooxidation of methylarenes to aromatic acetals

Peng Xiong, Huai-Bo Zhao, Xue-Ting Fan, Liang-Hua Jie, Hao Long, Pin Xu, Zhan-Jiang Liu, Zheng-Jian Wu, Jun Cheng () and Hai-Chao Xu ()
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Peng Xiong: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Huai-Bo Zhao: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Xue-Ting Fan: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Liang-Hua Jie: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Hao Long: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Pin Xu: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Zhan-Jiang Liu: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Zheng-Jian Wu: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Jun Cheng: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University
Hai-Chao Xu: Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: 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.

Date: 2020
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DOI: 10.1038/s41467-020-16519-8

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