Cathode Material Determines Product Selectivity for Electrochemical C−H Functionalization of Biaryl Ketoximes
The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wid...
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| Published in | Angewandte Chemie International Edition Vol. 57; no. 46; pp. 15153 - 15156 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
12.11.2018
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| Edition | International ed. in English |
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| Abstract | The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N‐heteroaromatic N‐oxides. The products of the electrosynthesis are switched to the deoxygenated N‐heteroaromatics by employing a Pb cathode through sequential anode‐promoted dehydrogenative cyclization and cathodic cleavage of the N−O bond in the initially formed N‐oxide.
Split personality: A divergent synthesis of polycyclic N‐heteroaromatics and the corresponding N‐oxides through electrochemical C−H functionalization of biaryl ketoximes has been developed. The choice of the cathode material controls product selectivity. |
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| AbstractList | The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N‐heteroaromatic N‐oxides. The products of the electrosynthesis are switched to the deoxygenated N‐heteroaromatics by employing a Pb cathode through sequential anode‐promoted dehydrogenative cyclization and cathodic cleavage of the N−O bond in the initially formed N‐oxide. The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N‐heteroaromatic N‐oxides. The products of the electrosynthesis are switched to the deoxygenated N‐heteroaromatics by employing a Pb cathode through sequential anode‐promoted dehydrogenative cyclization and cathodic cleavage of the N−O bond in the initially formed N‐oxide. Split personality: A divergent synthesis of polycyclic N‐heteroaromatics and the corresponding N‐oxides through electrochemical C−H functionalization of biaryl ketoximes has been developed. The choice of the cathode material controls product selectivity. The synthesis of polycyclic N-heteroaromatic compounds and their corresponding N-oxides has been developed through electrochemical C-H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N-heteroaromatic N-oxides. The products of the electrosynthesis are switched to the deoxygenated N-heteroaromatics by employing a Pb cathode through sequential anode-promoted dehydrogenative cyclization and cathodic cleavage of the N-O bond in the initially formed N-oxide. The synthesis of polycyclic N-heteroaromatic compounds and their corresponding N-oxides has been developed through electrochemical C-H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N-heteroaromatic N-oxides. The products of the electrosynthesis are switched to the deoxygenated N-heteroaromatics by employing a Pb cathode through sequential anode-promoted dehydrogenative cyclization and cathodic cleavage of the N-O bond in the initially formed N-oxide.The synthesis of polycyclic N-heteroaromatic compounds and their corresponding N-oxides has been developed through electrochemical C-H functionalization of biaryl ketoximes. The oxime substrates undergo dehydrogenative cyclization when a Pt cathode is used, resulting in unprecedented access to a wide range of N-heteroaromatic N-oxides. The products of the electrosynthesis are switched to the deoxygenated N-heteroaromatics by employing a Pb cathode through sequential anode-promoted dehydrogenative cyclization and cathodic cleavage of the N-O bond in the initially formed N-oxide. |
| Author | Zhao, Huai‐Bo Xu, Pin Song, Jinshuai Xu, Hai‐Chao |
| Author_xml | – sequence: 1 givenname: Huai‐Bo surname: Zhao fullname: Zhao, Huai‐Bo organization: Xiamen University – sequence: 2 givenname: Pin surname: Xu fullname: Xu, Pin organization: Xiamen University – sequence: 3 givenname: Jinshuai surname: Song fullname: Song, Jinshuai organization: Chinese Academy of Sciences – sequence: 4 givenname: Hai‐Chao orcidid: 0000-0002-3008-5143 surname: Xu fullname: Xu, Hai‐Chao email: haichao.xu@xmu.edu.cn organization: Xiamen University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30225909$$D View this record in MEDLINE/PubMed |
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| Issue | 46 |
| Keywords | radicals paired electrolysis C-H functionalization N-OXIDES oximes GREEN RADICAL FORMATION STRATEGIES METHODOLOGY heterocycles NITRILES GENERATION ORGANIC ELECTROSYNTHESIS C−H functionalization |
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| Snippet | The synthesis of polycyclic N‐heteroaromatic compounds and their corresponding N‐oxides has been developed through electrochemical C−H functionalization of... The synthesis of polycyclic N-heteroaromatic compounds and their corresponding N-oxides has been developed through electrochemical C-H functionalization of... |
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| SubjectTerms | Cathodes Chemistry Chemistry, Multidisciplinary C−H functionalization Dehydrogenation Deoxygenation Electrochemistry Electrode materials heterocycles Heterocyclic compounds Oxides oximes paired electrolysis Physical Sciences radicals Science & Technology Selectivity Substrates |
| Title | Cathode Material Determines Product Selectivity for Electrochemical C−H Functionalization of Biaryl Ketoximes |
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