Electrocatalytic ring-opening dihydroalkoxylation of N -aryl maleimides with alcohols under metal- and oxidant-free conditions
The electrocatalytic ring-opening dihydroalkoxylation of -aryl maleimides with alcohols under metal- and oxidant-free conditions is described. This electrochemical process consists of anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage and nucleophilic...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-04, Vol.21 (15), p.3177-3182 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Zhang, Zhang Wang, Ying-Chun Tang, Hai-Tao Pan, Ying-Ming Meng, Xiu-Jin |
| description | The electrocatalytic ring-opening dihydroalkoxylation of
-aryl maleimides with alcohols under metal- and oxidant-free conditions is described. This electrochemical process consists of anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage and nucleophilic addition cascade, which employs tetrabutylammonium bromide not only as a redox catalyst but also as an efficient supporting electrolyte, and offers a practical and environmentally friendly route to ring-opening difunctionalization products. |
| doi_str_mv | 10.1039/d3ob00178d |
| format | Article |
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-aryl maleimides with alcohols under metal- and oxidant-free conditions is described. This electrochemical process consists of anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage and nucleophilic addition cascade, which employs tetrabutylammonium bromide not only as a redox catalyst but also as an efficient supporting electrolyte, and offers a practical and environmentally friendly route to ring-opening difunctionalization products.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d3ob00178d</identifier><identifier>PMID: 36961319</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alcohols ; Anodizing ; Aromatic compounds ; Catalysts ; Electrochemistry ; Electron transfer ; Oxidants ; Oxidation ; Oxidizing agents ; Ring opening ; Single electrons ; Tetrabutylammonium bromide</subject><ispartof>Organic & biomolecular chemistry, 2023-04, Vol.21 (15), p.3177-3182</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c315t-4a9c80fd63a453f91f7b266046cc20a700cc105ad8e0e6f8c88591397c61d79f3</citedby><cites>FETCH-LOGICAL-c315t-4a9c80fd63a453f91f7b266046cc20a700cc105ad8e0e6f8c88591397c61d79f3</cites><orcidid>0000-0001-7662-7051 ; 0000-0001-7531-0458 ; 0000-0002-3625-7647</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36961319$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Zhang</creatorcontrib><creatorcontrib>Wang, Ying-Chun</creatorcontrib><creatorcontrib>Tang, Hai-Tao</creatorcontrib><creatorcontrib>Pan, Ying-Ming</creatorcontrib><creatorcontrib>Meng, Xiu-Jin</creatorcontrib><title>Electrocatalytic ring-opening dihydroalkoxylation of N -aryl maleimides with alcohols under metal- and oxidant-free conditions</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The electrocatalytic ring-opening dihydroalkoxylation of
-aryl maleimides with alcohols under metal- and oxidant-free conditions is described. This electrochemical process consists of anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage and nucleophilic addition cascade, which employs tetrabutylammonium bromide not only as a redox catalyst but also as an efficient supporting electrolyte, and offers a practical and environmentally friendly route to ring-opening difunctionalization products.</description><subject>Alcohols</subject><subject>Anodizing</subject><subject>Aromatic compounds</subject><subject>Catalysts</subject><subject>Electrochemistry</subject><subject>Electron transfer</subject><subject>Oxidants</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Ring opening</subject><subject>Single electrons</subject><subject>Tetrabutylammonium bromide</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0btOwzAUBmALgSi3hQdAllgQUsCOEzseoS0XCcECc-T6Ql0cu9iJoAvPjsttYDpn-PTr6PwAHGJ0hhHh54qEGUKYNWoD7OCKsQLVhG_-7SUagd2UFtlwRqttMCKUU0ww3wEfU6dlH4MUvXCr3koYrX8uwlL7PKGy85WKQbiX8L5yorfBw2DgPSxEXDnYCadtZ5VO8M32cyicDPPgEhy80hF2OocWUHgFw7tVwveFiVpDGbyy66y0D7aMcEkf_Mw98HQ1fRzfFHcP17fji7tCElz3RSW4bJBRlIiqJoZjw2YlpaiiUpZIMISkxKgWqtFIU9PIpqk5JpxJihXjhuyBk-_cZQyvg05929kktXPC6zCktmSZs7oueabH_-giDNHn69aKV_nPvMrq9FvJGFKK2rTLaLv8lBajdt1KOyEPl1-tTDI--okcZp1Wf_S3BvIJ-T6JCQ</recordid><startdate>20230412</startdate><enddate>20230412</enddate><creator>Zhang, Zhang</creator><creator>Wang, Ying-Chun</creator><creator>Tang, Hai-Tao</creator><creator>Pan, Ying-Ming</creator><creator>Meng, Xiu-Jin</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-7662-7051</orcidid><orcidid>https://orcid.org/0000-0001-7531-0458</orcidid><orcidid>https://orcid.org/0000-0002-3625-7647</orcidid></search><sort><creationdate>20230412</creationdate><title>Electrocatalytic ring-opening dihydroalkoxylation of N -aryl maleimides with alcohols under metal- and oxidant-free conditions</title><author>Zhang, Zhang ; Wang, Ying-Chun ; Tang, Hai-Tao ; Pan, Ying-Ming ; Meng, Xiu-Jin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c315t-4a9c80fd63a453f91f7b266046cc20a700cc105ad8e0e6f8c88591397c61d79f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alcohols</topic><topic>Anodizing</topic><topic>Aromatic compounds</topic><topic>Catalysts</topic><topic>Electrochemistry</topic><topic>Electron transfer</topic><topic>Oxidants</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Ring opening</topic><topic>Single electrons</topic><topic>Tetrabutylammonium bromide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhang</creatorcontrib><creatorcontrib>Wang, Ying-Chun</creatorcontrib><creatorcontrib>Tang, Hai-Tao</creatorcontrib><creatorcontrib>Pan, Ying-Ming</creatorcontrib><creatorcontrib>Meng, Xiu-Jin</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zhang</au><au>Wang, Ying-Chun</au><au>Tang, Hai-Tao</au><au>Pan, Ying-Ming</au><au>Meng, Xiu-Jin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrocatalytic ring-opening dihydroalkoxylation of N -aryl maleimides with alcohols under metal- and oxidant-free conditions</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-04-12</date><risdate>2023</risdate><volume>21</volume><issue>15</issue><spage>3177</spage><epage>3182</epage><pages>3177-3182</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The electrocatalytic ring-opening dihydroalkoxylation of
-aryl maleimides with alcohols under metal- and oxidant-free conditions is described. This electrochemical process consists of anodic single-electron transfer oxidation, cathodic radical reduction, rearrangement-ring cleavage and nucleophilic addition cascade, which employs tetrabutylammonium bromide not only as a redox catalyst but also as an efficient supporting electrolyte, and offers a practical and environmentally friendly route to ring-opening difunctionalization products.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36961319</pmid><doi>10.1039/d3ob00178d</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0001-7662-7051</orcidid><orcidid>https://orcid.org/0000-0001-7531-0458</orcidid><orcidid>https://orcid.org/0000-0002-3625-7647</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-04, Vol.21 (15), p.3177-3182 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohols Anodizing Aromatic compounds Catalysts Electrochemistry Electron transfer Oxidants Oxidation Oxidizing agents Ring opening Single electrons Tetrabutylammonium bromide |
| title | Electrocatalytic ring-opening dihydroalkoxylation of N -aryl maleimides with alcohols under metal- and oxidant-free conditions |
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