Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones
A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation we...
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| Veröffentlicht in: | Organic letters 2017-12, Vol.19 (24), p.6622-6625 |
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| container_end_page | 6625 |
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| container_issue | 24 |
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| container_title | Organic letters |
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| creator | Zhang, Sheng Lian, Fei Xue, Mengyu Qin, Tengteng Li, Lijun Zhang, Xu Xu, Kun |
| description | A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural product cytosporanone A on a gram scale. |
| doi_str_mv | 10.1021/acs.orglett.7b03333 |
| format | Article |
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With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural product cytosporanone A on a gram scale.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.7b03333</identifier><identifier>PMID: 29185759</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemical synthesis ; Benzophenones - chemical synthesis ; Carboxylic Acids - chemistry ; Catalysis ; Electrochemical Techniques ; Esterification ; Lactones - chemistry ; Oxidation-Reduction</subject><ispartof>Organic letters, 2017-12, Vol.19 (24), p.6622-6625</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a411t-c41e601b7729631cae5f8745b369cc30b5884b51297b9829cd0113f56a294dda3</citedby><cites>FETCH-LOGICAL-a411t-c41e601b7729631cae5f8745b369cc30b5884b51297b9829cd0113f56a294dda3</cites><orcidid>0000-0002-9686-3921 ; 0000-0002-3588-3240 ; 0000-0002-0419-8822</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b03333$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.7b03333$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29185759$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Sheng</creatorcontrib><creatorcontrib>Lian, Fei</creatorcontrib><creatorcontrib>Xue, Mengyu</creatorcontrib><creatorcontrib>Qin, Tengteng</creatorcontrib><creatorcontrib>Li, Lijun</creatorcontrib><creatorcontrib>Zhang, Xu</creatorcontrib><creatorcontrib>Xu, Kun</creatorcontrib><title>Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural product cytosporanone A on a gram scale.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemical synthesis</subject><subject>Benzophenones - chemical synthesis</subject><subject>Carboxylic Acids - chemistry</subject><subject>Catalysis</subject><subject>Electrochemical Techniques</subject><subject>Esterification</subject><subject>Lactones - chemistry</subject><subject>Oxidation-Reduction</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kF1PwyAYhYnRuDn9BSaml95046O0xbs550eyxBu9JpTSjcnKBGrsv5e5uUu54Lwh5xzyPgBcIzhGEKOJkH5s3dKoEMZFBUk8J2CIKCZpASk-Pc45HIAL79cQovjCzsEAM1TSgrIh-JgbJYOzUgRh-qBl8qBWfe3sUrUi6C-VzH1QTjc6OrRtE9skU6O3K7HzzoSr7Hdv4jiVuvZ3UaTyPgk2uddWyN-GRVTbKn8JzhphvLo66Ai8P87fZs_p4vXpZTZdpCJDKKQyQyqHqCoKzHKCpFC0KYuMViRnUhJY0bLMKoowKypWYibruBdpaC4wy-pakBG43fdunf3slA98o71UxohW2c5zxCITQlC8RoDsrdJZ751q-NbpjXA9R5DvKPNImR8o8wPlmLo5fNBVG1UfM39Yo2GyN-zSa9u5Nu77b-UPtt-MlA</recordid><startdate>20171215</startdate><enddate>20171215</enddate><creator>Zhang, Sheng</creator><creator>Lian, Fei</creator><creator>Xue, Mengyu</creator><creator>Qin, Tengteng</creator><creator>Li, Lijun</creator><creator>Zhang, Xu</creator><creator>Xu, Kun</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9686-3921</orcidid><orcidid>https://orcid.org/0000-0002-3588-3240</orcidid><orcidid>https://orcid.org/0000-0002-0419-8822</orcidid></search><sort><creationdate>20171215</creationdate><title>Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones</title><author>Zhang, Sheng ; Lian, Fei ; Xue, Mengyu ; Qin, Tengteng ; Li, Lijun ; Zhang, Xu ; Xu, Kun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a411t-c41e601b7729631cae5f8745b369cc30b5884b51297b9829cd0113f56a294dda3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - chemical synthesis</topic><topic>Benzophenones - chemical synthesis</topic><topic>Carboxylic Acids - chemistry</topic><topic>Catalysis</topic><topic>Electrochemical Techniques</topic><topic>Esterification</topic><topic>Lactones - chemistry</topic><topic>Oxidation-Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Sheng</creatorcontrib><creatorcontrib>Lian, Fei</creatorcontrib><creatorcontrib>Xue, Mengyu</creatorcontrib><creatorcontrib>Qin, Tengteng</creatorcontrib><creatorcontrib>Li, Lijun</creatorcontrib><creatorcontrib>Zhang, Xu</creatorcontrib><creatorcontrib>Xu, Kun</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Sheng</au><au>Lian, Fei</au><au>Xue, Mengyu</au><au>Qin, Tengteng</au><au>Li, Lijun</au><au>Zhang, Xu</au><au>Xu, Kun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2017-12-15</date><risdate>2017</risdate><volume>19</volume><issue>24</issue><spage>6622</spage><epage>6625</epage><pages>6622-6625</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A scalable and efficient electrocatalytic dehydrogenative esterification is reported. With an indirect electrolysis strategy, both intra- and intermolecular-type reactions were amenable to this practical method. With n-Bu4NI as the catalyst, undesired decarboxylation and Baeyer–Villiger oxidation were suppressed. More importantly, this novel method provided reliable and direct access to the natural product cytosporanone A on a gram scale.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>29185759</pmid><doi>10.1021/acs.orglett.7b03333</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-9686-3921</orcidid><orcidid>https://orcid.org/0000-0002-3588-3240</orcidid><orcidid>https://orcid.org/0000-0002-0419-8822</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2017-12, Vol.19 (24), p.6622-6625 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemical synthesis Benzophenones - chemical synthesis Carboxylic Acids - chemistry Catalysis Electrochemical Techniques Esterification Lactones - chemistry Oxidation-Reduction |
| title | Electrocatalytic Dehydrogenative Esterification of Aliphatic Carboxylic Acids: Access to Bioactive Lactones |
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