Details

Autor(en) / Beteiligte

• Xiong, Peng
• Zhao, Huai-Bo
• Fan, Xue-Ting
• Jie, Liang-Hua
• Long, Hao
• Xu, Pin
• Liu, Zhan-Jiang
• Wu, Zheng-Jian
• Cheng, Jun
• Xu, Hai-Chao

Titel

Site-selective electrooxidation of methylarenes to aromatic acetals

Ist Teil von

• Nature communications, 2020-06, Vol.11 (1), p.1-8, Article 2706

Ort / Verlag

London: Nature Publishing Group

Erscheinungsjahr

2020

Quelle

EZB-FREE-00999 freely available EZB journals

Beschreibungen/Notizen

• 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.