Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates
Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. The reaction of 2,4,4-trisubstitute...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2010-01, Vol.8 (1), p.274-281 |
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| creator | Lü, Bo Fu, Chunling Ma, Shengming |
| description | Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed. |
| doi_str_mv | 10.1039/b917793k |
| format | Article |
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The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b917793k</identifier><identifier>PMID: 20024159</identifier><language>eng</language><publisher>England</publisher><subject>4-Butyrolactone - analogs & derivatives ; 4-Butyrolactone - chemical synthesis ; 4-Butyrolactone - chemistry ; Diazonium Compounds - chemistry ; Molecular Structure ; Phenylbutyrates - chemical synthesis ; Phenylbutyrates - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2010-01, Vol.8 (1), p.274-281</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c282t-d2059c031fd6ef8836e7cfb5826ff05e43dd70fb532553fac427b68148d2d4ac3</citedby><cites>FETCH-LOGICAL-c282t-d2059c031fd6ef8836e7cfb5826ff05e43dd70fb532553fac427b68148d2d4ac3</cites></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/20024159$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lü, Bo</creatorcontrib><creatorcontrib>Fu, Chunling</creatorcontrib><creatorcontrib>Ma, Shengming</creatorcontrib><title>Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. The reaction of 2,4,4-trisubstituted 2,3-allenoates afforded the corresponding 4-fluoro-2(5H)-furanones highly selectively with up to 95% yield under different conditions. The scope of the substrates has been carefully explored. Due to the more readily availability of 2,3-allenoates as compared to 2,3-allenoic acids, new 4-fluoro-2(5H)-furanones were prepared. Based on the isolation and characterization of the minor fluorohydroxylation product E-5m, a mechanism has been proposed.</description><subject>4-Butyrolactone - analogs & derivatives</subject><subject>4-Butyrolactone - chemical synthesis</subject><subject>4-Butyrolactone - chemistry</subject><subject>Diazonium Compounds - chemistry</subject><subject>Molecular Structure</subject><subject>Phenylbutyrates - chemical synthesis</subject><subject>Phenylbutyrates - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kclOwzAURS0EgjJIfAHyjlbC4Clxwg4qJlGJRWEduR5UQ2qX2AH6Z3we6UBX7-m-c-9bXABOCb4kmJVXk5IIUbKPHdAjXAiEM1bubneKD8BhjO8Yk1LkfB8cUIwpJ1nZA7_j1OoFDB6mqYHR1EYl9-XSArq1tFKaMJ-62ik4Cz7Yug2N8zK5zhUspBcMybo2PshkIvx2aQrHK9uKvIbSQ2OtU874BOPCd7HRxaWVoxUSEO1njwNk20b64LsQ6TVk_0eOws8SuRt0fz42f47BnpV1NCebeQTe7u9eh49o9PLwNLwZIUULmpCmOCsVZsTq3NiiYLkRyk6ygubW4sxwprXAncBoljErFadikheEF5pqLhU7Aufr3HkTPlsTUzVzUZm6lt6ENlaCsRyXouAd2V-TqgkxNsZW88bNZLOoCK6WNVW365qeO_RsE9pOZkZvwf9e2B_hT48g</recordid><startdate>20100101</startdate><enddate>20100101</enddate><creator>Lü, Bo</creator><creator>Fu, Chunling</creator><creator>Ma, Shengming</creator><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></search><sort><creationdate>20100101</creationdate><title>Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates</title><author>Lü, Bo ; Fu, Chunling ; Ma, Shengming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c282t-d2059c031fd6ef8836e7cfb5826ff05e43dd70fb532553fac427b68148d2d4ac3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>4-Butyrolactone - analogs & derivatives</topic><topic>4-Butyrolactone - chemical synthesis</topic><topic>4-Butyrolactone - chemistry</topic><topic>Diazonium Compounds - chemistry</topic><topic>Molecular Structure</topic><topic>Phenylbutyrates - chemical synthesis</topic><topic>Phenylbutyrates - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lü, Bo</creatorcontrib><creatorcontrib>Fu, Chunling</creatorcontrib><creatorcontrib>Ma, Shengming</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 & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lü, Bo</au><au>Fu, Chunling</au><au>Ma, Shengming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2010-01-01</date><risdate>2010</risdate><volume>8</volume><issue>1</issue><spage>274</spage><epage>281</epage><pages>274-281</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Different from the reaction of 2,3-allenoic acids with Selectfluor, 4-fluoro-2(5H)-furanones and (E)-3-fluoro-4-oxo-2-alkenoates were highly selectively generated from 2,4-disubstituted 2,3-allenoates with Selectfluor under different conditions in moderate yields. 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| ispartof | Organic & biomolecular chemistry, 2010-01, Vol.8 (1), p.274-281 |
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| language | eng |
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| source | MEDLINE; Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| subjects | 4-Butyrolactone - analogs & derivatives 4-Butyrolactone - chemical synthesis 4-Butyrolactone - chemistry Diazonium Compounds - chemistry Molecular Structure Phenylbutyrates - chemical synthesis Phenylbutyrates - chemistry |
| title | Study on the selectivity in the electrophilic monofluorination of 2,3-allenoates with Selectfluor: an efficient synthesis of 4-fluoro-2(5H)-furanones and 3-fluoro-4-oxo-2(E)-alkenoates |
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