An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor
The internal CC double bond in 3-aryl-1,2-allenes was highly regioselectively fluorohydroxylated to afford 2-fluoroalken-3-ols in 37−88% yields by using Selectfluor as the electrophilic reagent. The regioselectivity may be determined by the electronic effect, while the reactivity may be controlled...
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| Veröffentlicht in: | Organic letters 2008-02, Vol.10 (4), p.581-583 |
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| container_end_page | 583 |
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| container_title | Organic letters |
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| creator | Zhou, Chao Li, Jing Lü, Bo Fu, Chunling Ma, Shengming |
| description | The internal CC double bond in 3-aryl-1,2-allenes was highly regioselectively fluorohydroxylated to afford 2-fluoroalken-3-ols in 37−88% yields by using Selectfluor as the electrophilic reagent. The regioselectivity may be determined by the electronic effect, while the reactivity may be controlled by the stabilization effect of the aryl group in the allylic cationic intermediates. |
| doi_str_mv | 10.1021/ol702863n |
| format | Article |
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The regioselectivity may be determined by the electronic effect, while the reactivity may be controlled by the stabilization effect of the aryl group in the allylic cationic intermediates.</description><subject>Alkadienes - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Diazonium Compounds - chemistry</subject><subject>Fluorine - chemistry</subject><subject>Hydroxylation</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtKAzEUhoMotl4WvoBkoyA4moszk1mWUi-gCOp-SJMTG0mTmsxU5w18bMe26MbV-Tl8_IfzIXREyQUljF4GVxImCu630JDmjGclydn2by7IAO2l9EYI7TfVLhpQQSsuBBmir5HHE2OssuAbPFosYpBqhk2I-CH4YFwbovWyscHjpZX41r7OXIef4NWGBA5UY5eAr3-wMOt0DJ-dW9NPINUqBIN5Noqdy-g5y6Rz4CHhD9vM8POqYXXkAO0Y6RIcbuY-ermevIxvs_vHm7vx6D6TnPImY6WWgnIoNKUSFJeFvBJUKFKYSmiZV7wwuhQ5hym5mmoNmkFFSsZYLimUfB-drmv7R99bSE09t0mBc9JDaFPdiyw5yXkPnq1BFUNKEUy9iHYuY1dTUv9Yr3-t9-zxprSdzkH_kRvNPXCyBqRK9Vtoo-9f_KfoG5QOi2Q</recordid><startdate>20080221</startdate><enddate>20080221</enddate><creator>Zhou, Chao</creator><creator>Li, Jing</creator><creator>Lü, Bo</creator><creator>Fu, Chunling</creator><creator>Ma, Shengming</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></search><sort><creationdate>20080221</creationdate><title>An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor</title><author>Zhou, Chao ; Li, Jing ; Lü, Bo ; Fu, Chunling ; Ma, Shengming</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-27da813e6d11aec3a6a4818c06f98da5936fd7853eb04bdded2e9072225a1e73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Alkadienes - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Diazonium Compounds - chemistry</topic><topic>Fluorine - chemistry</topic><topic>Hydroxylation</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Chao</creatorcontrib><creatorcontrib>Li, Jing</creatorcontrib><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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Chao</au><au>Li, Jing</au><au>Lü, Bo</au><au>Fu, Chunling</au><au>Ma, Shengming</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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| ispartof | Organic letters, 2008-02, Vol.10 (4), p.581-583 |
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| language | eng |
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| source | MEDLINE; ACS Publications |
| subjects | Alkadienes - chemistry Catalysis Cyclization Diazonium Compounds - chemistry Fluorine - chemistry Hydroxylation Molecular Structure Stereoisomerism |
| title | An Efficient Approach for Monofluorination via Highly Regioselective Fluorohydroxylation Reaction of 3-Aryl-1,2-allenes with Selectfluor |
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