Site-selective electrooxidation of methylarenes to aromatic acetals
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 m...
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| Published in | Nature communications Vol. 11; no. 1; pp. 2706 - 8 |
|---|---|
| Main Authors | , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
01.06.2020
Nature Publishing Group Nature Portfolio |
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| Online Access | Get full text |
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| 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.
Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts. |
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| AbstractList | 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.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. Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts. 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. Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts. 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. 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.Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an electrochemical, site-selective method for the oxidation of methyl benzoheterocycles to aromatic acetals without using chemical oxidants or transition metal catalysts. |
| ArticleNumber | 2706 |
| Author | Jie, Liang-Hua Xiong, Peng Xu, Pin Zhao, Huai-Bo Wu, Zheng-Jian Long, Hao Xu, Hai-Chao Fan, Xue-Ting Liu, Zhan-Jiang Cheng, Jun |
| Author_xml | – sequence: 1 givenname: Peng surname: Xiong fullname: Xiong, Peng organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 2 givenname: Huai-Bo surname: Zhao fullname: Zhao, Huai-Bo organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 3 givenname: Xue-Ting surname: Fan fullname: Fan, Xue-Ting organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 4 givenname: Liang-Hua surname: Jie fullname: Jie, Liang-Hua organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 5 givenname: Hao surname: Long fullname: Long, Hao organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 6 givenname: Pin surname: Xu fullname: Xu, Pin organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 7 givenname: Zhan-Jiang surname: Liu fullname: Liu, Zhan-Jiang organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 8 givenname: Zheng-Jian surname: Wu fullname: Wu, Zheng-Jian organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 9 givenname: Jun orcidid: 0000-0001-6971-0797 surname: Cheng fullname: Cheng, Jun email: chengjun@xmu.edu.cn organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University – sequence: 10 givenname: Hai-Chao orcidid: 0000-0002-3008-5143 surname: Xu fullname: Xu, Hai-Chao email: haichao.xu@xmu.edu.cn organization: State Key Laboratory of Physical Chemistry of Solid Surfaces, Innovative Collaboration Center of Chemistry for Energy Materials, and College of Chemistry and Chemical Engineering, Xiamen University, Key Laboratory of Chemical Biology of Fujian Province, Xiamen University |
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| Snippet | Aldehyde is one of most synthetically versatile functional groups and can participate in numerous chemical transformations. While a variety of simple aromatic... Benzylic oxygenation of methylarenes is a direct but challenging method for aldehyde synthesis from simple starting materials. Here, the authors show an... |
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| SubjectTerms | 119/118 140/131 140/58 639/638/161 639/638/403/933 639/638/549 Acetals Aldehydes Antihypertensives Catalysts Electrochemistry Functional groups Humanities and Social Sciences multidisciplinary Oxidants Oxidation Oxidizing agents Oxygenation Science Science (multidisciplinary) Synthesis Transition metals |
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| Title | Site-selective electrooxidation of methylarenes to aromatic acetals |
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