Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes
Identifieur interne : 001722 ( Istex/Corpus ); précédent : 001721; suivant : 001723Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes
Auteurs : Krzysztof Durka ; Krzysztof Gontarczyk ; Tomasz Kli ; Janusz Serwatowski ; Krzysztof Wo NiakSource :
- Applied Organometallic Chemistry [ 0268-2605 ] ; 2012-06.
English descriptors
- KwdEn :
- Acta cryst, Anal, Appl, Aryllithiums, Benzylic, Benzylic hydrogen, Benzylic position, Boronic, Boronic acid, Boronic acids, Calcd, Cbenz, Cdcl3, Chem, Copyright, Cyano, Cyano group, Deprotonation, Equiv, John wiley sons, Lithiation, Me3sicl, Oxygen atoms, Phenyl ring, Reaction conditions, Uorine, Uorine atoms, Warsaw university.
- Teeft :
- Acta cryst, Anal, Appl, Aryllithiums, Benzylic, Benzylic hydrogen, Benzylic position, Boronic, Boronic acid, Boronic acids, Calcd, Cbenz, Cdcl3, Chem, Copyright, Cyano, Cyano group, Deprotonation, Equiv, John wiley sons, Lithiation, Me3sicl, Oxygen atoms, Phenyl ring, Reaction conditions, Uorine, Uorine atoms, Warsaw university.
Abstract
Lithium diisopropylamine (LDA)‐mediated deprotonation reactions of halogenated cyanobenzyloxy‐benzenes and cyanobiphenyls were investigated. The resultant organolithium derivatives were converted into the corresponding arylboronic acids or silanes. It was found that the stability of the obtained aryllithiums towards isomerization to the respective benzyllithiums depends strongly on the number of fluorine atoms in the phenyl ring and on the position of the cyano group. Halogenated cyanobiaryls were selectively deprotonated in the position flanked by two halogen atoms; however, the yield depended strongly on the reaction conditions. Addition of LDA to the cyano group was observed on the lithiation of 4‐cyano‐3′,5′‐dichlorobiphenyl rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.
Url:
DOI: 10.1002/aoc.2856
Links to Exploration step
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<front><div type="abstract">Lithium diisopropylamine (LDA)‐mediated deprotonation reactions of halogenated cyanobenzyloxy‐benzenes and cyanobiphenyls were investigated. The resultant organolithium derivatives were converted into the corresponding arylboronic acids or silanes. It was found that the stability of the obtained aryllithiums towards isomerization to the respective benzyllithiums depends strongly on the number of fluorine atoms in the phenyl ring and on the position of the cyano group. Halogenated cyanobiaryls were selectively deprotonated in the position flanked by two halogen atoms; however, the yield depended strongly on the reaction conditions. Addition of LDA to the cyano group was observed on the lithiation of 4‐cyano‐3′,5′‐dichlorobiphenyl rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.</div>
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<profileDesc><abstract style="main"><p>Lithium diisopropylamine (LDA)‐mediated <term type="reactionType">deprotonation reactions</term>
of halogenated cyanobenzyloxy‐benzenes and cyanobiphenyls were investigated. The resultant organolithium derivatives were converted into the corresponding arylboronic acids or silanes. It was found that the stability of the obtained aryllithiums towards isomerization to the respective benzyllithiums depends strongly on the number of fluorine atoms in the phenyl ring and on the position of the cyano group. Halogenated cyanobiaryls were selectively deprotonated in the position flanked by two halogen atoms; however, the yield depended strongly on the reaction conditions. Addition of LDA to the cyano group was observed on the <term type="reactionType">lithiation</term>
of <term type="chemicalName" xml:id="aoc2856-info-0002">4‐cyano‐3′,5′‐dichlorobiphenyl</term>
rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.</p>
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<abstract style="graphical"><p>Cyanoarylboronic acids and silanes have been obtained by lithiation of aryloxymethyl‐benzonitriles or dihalogeno‐cyanobiphenyls and the subsequent reaction with B(OR)<hi rend="subscript">3</hi>
or Me<hi rend="subscript">3</hi>
SiCl. The stability of the obtained cyano‐aryllithiums depends on the position of the cyano group and the number of fluorine atoms in the phenyl ring
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<abstractGroup><abstract type="main"><p>Lithium diisopropylamine (LDA)‐mediated <infoAsset type="reactionType">deprotonation reactions</infoAsset>
of halogenated cyanobenzyloxy‐benzenes and cyanobiphenyls were investigated. The resultant organolithium derivatives were converted into the corresponding arylboronic acids or silanes. It was found that the stability of the obtained aryllithiums towards isomerization to the respective benzyllithiums depends strongly on the number of fluorine atoms in the phenyl ring and on the position of the cyano group. Halogenated cyanobiaryls were selectively deprotonated in the position flanked by two halogen atoms; however, the yield depended strongly on the reaction conditions. Addition of LDA to the cyano group was observed on the <infoAsset type="reactionType">lithiation</infoAsset>
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rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.</p>
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<abstract type="graphical"><p>Cyanoarylboronic acids and silanes have been obtained by lithiation of aryloxymethyl‐benzonitriles or dihalogeno‐cyanobiphenyls and the subsequent reaction with B(OR)<sub>3</sub>
or Me<sub>3</sub>
SiCl. The stability of the obtained cyano‐aryllithiums depends on the position of the cyano group and the number of fluorine atoms in the phenyl ring
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<titleInfo type="alternative" contentType="CDATA" lang="en"><title>Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes</title>
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<name type="personal"><namePart type="given">Krzysztof</namePart>
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<name type="personal"><namePart type="given">Tomasz</namePart>
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<affiliation>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw, Poland</affiliation>
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<abstract>Lithium diisopropylamine (LDA)‐mediated deprotonation reactions of halogenated cyanobenzyloxy‐benzenes and cyanobiphenyls were investigated. The resultant organolithium derivatives were converted into the corresponding arylboronic acids or silanes. It was found that the stability of the obtained aryllithiums towards isomerization to the respective benzyllithiums depends strongly on the number of fluorine atoms in the phenyl ring and on the position of the cyano group. Halogenated cyanobiaryls were selectively deprotonated in the position flanked by two halogen atoms; however, the yield depended strongly on the reaction conditions. Addition of LDA to the cyano group was observed on the lithiation of 4‐cyano‐3′,5′‐dichlorobiphenyl rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.</abstract>
<abstract type="graphical">Cyanoarylboronic acids and silanes have been obtained by lithiation of aryloxymethyl‐benzonitriles or dihalogeno‐cyanobiphenyls and the subsequent reaction with B(OR)3 or Me3SiCl. The stability of the obtained cyano‐aryllithiums depends on the position of the cyano group and the number of fluorine atoms in the phenyl ring</abstract>
<subject><genre>keywords</genre>
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<topic>nitriles</topic>
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<identifier type="eISSN">1099-0739</identifier>
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<part><date>2012</date>
<detail type="volume"><caption>vol.</caption>
<number>26</number>
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