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
ISTEX:F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5Le document en format XML
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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. 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target="urn:x-wiley:02682605:media:AOC2856:aoc2856-fig-0004_templated_Structure_#_0001_"></ref></edition></editionStmt><publicationStmt><authority>ISTEX</authority><publisher>John Wiley & Sons, Ltd</publisher><pubPlace>Chichester, UK</pubPlace><availability><licence>Copyright © 2012 John Wiley & Sons, Ltd.</licence></availability><date type="published" when="2012-06"></date></publicationStmt><notesStmt><note type="content-type" subtype="article" source="article" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</note><note type="publication-type" subtype="journal" scheme="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</note></notesStmt><sourceDesc><biblStruct type="article"><analytic><title level="a" type="main">Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes</title><title level="a" type="short">Stability of some aryllithiums in the presence of cyano group</title><author xml:id="author-0000"><persName><forename type="first">Krzysztof</forename><surname>Durka</surname></persName><affiliation><orgName>Faculty of Chemistry</orgName><orgName>Warsaw University of Technology</orgName><address><settlement type="city">Warsaw</settlement><postCode>00‐664</postCode><country key="PL">Poland</country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Krzysztof</forename><surname>Gontarczyk</surname></persName><affiliation><orgName>Faculty of Chemistry</orgName><orgName>Warsaw University of Technology</orgName><address><settlement type="city">Warsaw</settlement><postCode>00‐664</postCode><country key="PL">Poland</country></address></affiliation></author><author xml:id="author-0002" role="corresp"><persName><forename type="first">Tomasz</forename><surname>Kliś</surname></persName><email>ktom@ch.pw.edu.pl</email><affiliation><orgName>Faculty of Chemistry</orgName><orgName>Warsaw University of Technology</orgName><address><settlement type="city">Warsaw</settlement><postCode>00‐664</postCode><country key="PL">Poland</country></address></affiliation><affiliation>Tomasz Kliś, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00–664 Warsaw, Poland. E‐mail: ktom@ch.pw.edu.pl</affiliation></author><author xml:id="author-0003"><persName><forename type="first">Janusz</forename><surname>Serwatowski</surname></persName><affiliation><orgName>Faculty of Chemistry</orgName><orgName>Warsaw University of Technology</orgName><address><settlement type="city">Warsaw</settlement><postCode>00‐664</postCode><country key="PL">Poland</country></address></affiliation></author><author xml:id="author-0004"><persName><forename type="first">Krzysztof</forename><surname>Woźniak</surname></persName><affiliation><orgName>Faculty of Chemistry</orgName><orgName>Warsaw University</orgName><address><settlement type="city">Warsaw</settlement><postCode>02‐093</postCode><country key="PL">Poland</country></address></affiliation></author><idno type="istex">F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5</idno><idno type="ark">ark:/67375/WNG-QPP9XRK2-V</idno><idno type="DOI">10.1002/aoc.2856</idno><idno type="unit">AOC2856</idno><idno type="toTypesetVersion">file:AOC.AOC2856.pdf</idno></analytic><monogr><title level="j" type="main">Applied Organometallic Chemistry</title><title level="j" type="alt">APPLIED ORGANOMETALLIC CHEMISTRY</title><idno type="pISSN">0268-2605</idno><idno type="eISSN">1099-0739</idno><idno type="book-DOI">10.1002/(ISSN)1099-0739</idno><idno type="book-part-DOI">10.1002/aoc.v26.6</idno><idno type="product">AOC</idno><imprint><biblScope unit="vol">26</biblScope><biblScope unit="issue">6</biblScope><biblScope unit="page" from="287">287</biblScope><biblScope unit="page" to="292">292</biblScope><biblScope unit="page-count">6</biblScope><publisher>John Wiley & Sons, Ltd</publisher><pubPlace>Chichester, UK</pubPlace><date type="published" when="2012-06"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><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></abstract><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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Organometal. Chem.</title></titleGroup></publicationMeta><publicationMeta level="part" position="60"><doi>10.1002/aoc.v26.6</doi><copyright ownership="publisher">Copyright © 2012 John Wiley & Sons, Ltd.</copyright><numberingGroup><numbering number="26" type="journalVolume">26</numbering><numbering type="journalIssue">6</numbering></numberingGroup><coverDate startDate="2012-06">June 2012</coverDate></publicationMeta><publicationMeta level="unit" position="60" status="forIssue" type="article"><doi>10.1002/aoc.2856</doi><idGroup><id type="unit" value="AOC2856"></id></idGroup><countGroup><count number="6" type="pageTotal"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title><title type="tocHeading1">Full Papers</title></titleGroup><copyright ownership="publisher">Copyright © 2012 John Wiley & Sons, Ltd.</copyright><eventGroup><event date="2012-01-09" type="manuscriptReceived"></event><event date="2012-03-09" type="manuscriptRevised"></event><event date="2012-03-09" type="manuscriptAccepted"></event><event agent="SPi Global" date="2012-04-02" type="xmlCreated"></event><event date="2012-05-09" type="publishedOnlineEarlyUnpaginated"></event><event date="2012-05-09" type="firstOnline"></event><event date="2012-05-28" type="publishedOnlineFinalForm"></event><event agent="Converter:wiley:ML3G_TO_wiley:ML3GV2 version:3.1.5 mode:FullText" date="2012-06-13" type="xmlConverted"></event><event agent="InfoChem" date="2012-07-09" type="xmlEnhanced"></event><event agent="PQA_Process" date="2012-10-01" type="xmlEnhanced"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.3.4 mode:FullText" date="2015-02-24"></event></eventGroup><numberingGroup><numbering type="pageFirst">287</numbering><numbering type="pageLast">292</numbering></numberingGroup><correspondenceTo>Tomasz Kliś, Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00–664 Warsaw, Poland. 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xml:id="aoc2856-eo-0053"><mediaResourceGroup><mediaResource alt="chemical compound" copyright="John Wiley & Sons, Ltd." eRights="yes" href="urn:x-wiley:02682605:media:AOC2856:aoc2856-fig-0004_templated_Structure_#_0000_"></mediaResource></mediaResourceGroup></enrichedObject><enrichedObject associatedDataRef="#aoc2856-fig-0004" relevance="secondary" xml:id="aoc2856-eo-0054"><mediaResourceGroup><mediaResource alt="chemical compound" copyright="John Wiley & Sons, Ltd." eRights="yes" href="urn:x-wiley:02682605:media:AOC2856:aoc2856-fig-0004_templated_Structure_#_0001_"></mediaResource></mediaResourceGroup></enrichedObject></enrichedObjectGroup><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> of <infoAsset type="chemicalName" xml:id="aoc2856-info-0002">4‐cyano‐3′,5′‐dichlorobiphenyl</infoAsset> rather than deprotonation. Copyright © 2012 John Wiley & Sons, Ltd.</p></abstract><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
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" href="urn:x-wiley:02682605:media:aoc2856:aoc2856-toc-0001"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Stability of some aryllithiums in the presence of cyano group</title></titleInfo><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></titleInfo><name type="personal"><namePart type="given">Krzysztof</namePart><namePart type="family">Durka</namePart><affiliation>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Krzysztof</namePart><namePart type="family">Gontarczyk</namePart><affiliation>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Tomasz</namePart><namePart type="family">Kliś</namePart><affiliation>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw, Poland</affiliation><affiliation>E-mail: ktom@ch.pw.edu.pl</affiliation><affiliation>E-mail: ktom@ch.pw.edu.pl</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Janusz</namePart><namePart type="family">Serwatowski</namePart><affiliation>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Krzysztof</namePart><namePart type="family">Woźniak</namePart><affiliation>Faculty of Chemistry, Warsaw University, 02‐093, Warsaw, Poland</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>John Wiley & Sons, Ltd</publisher><place><placeTerm type="text">Chichester, UK</placeTerm></place><dateIssued encoding="w3cdtf">2012-06</dateIssued><dateCreated encoding="w3cdtf">2012-04-02</dateCreated><dateCaptured encoding="w3cdtf">2012-01-09</dateCaptured><dateValid encoding="w3cdtf">2012-03-09</dateValid><copyrightDate encoding="w3cdtf">2012</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><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><topic>lithiation</topic><topic>nitriles</topic><topic>boronic acids</topic><topic>silanes</topic></subject><relatedItem type="host"><titleInfo><title>Applied Organometallic Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>Appl. Organometal. Chem.</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><subject><genre>article-category</genre><topic>Full Paper</topic></subject><identifier type="ISSN">0268-2605</identifier><identifier type="eISSN">1099-0739</identifier><identifier type="DOI">10.1002/(ISSN)1099-0739</identifier><identifier type="PublisherID">AOC</identifier><part><date>2012</date><detail type="volume"><caption>vol.</caption><number>26</number></detail><detail type="issue"><caption>no.</caption><number>6</number></detail><extent unit="pages"><start>287</start><end>292</end><total>6</total></extent></part></relatedItem><identifier type="istex">F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5</identifier><identifier type="ark">ark:/67375/WNG-QPP9XRK2-V</identifier><identifier type="DOI">10.1002/aoc.2856</identifier><identifier type="ArticleID">AOC2856</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2012 John Wiley & Sons, Ltd.Copyright © 2012 John Wiley & Sons, Ltd.</accessCondition><recordInfo><recordContentSource authority="ISTEX" authorityURI="https://loaded-corpus.data.istex.fr" valueURI="https://loaded-corpus.data.istex.fr/ark:/67375/XBH-L0C46X92-X">wiley</recordContentSource><recordOrigin>John Wiley & Sons, Ltd</recordOrigin></recordInfo></mods><json:item><extension>json</extension><original>false</original><mimetype>application/json</mimetype><uri>https://api.istex.fr/document/F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5/metadata/json</uri></json:item></metadata><serie></serie></istex></record>Pour manipuler ce document sous Unix (Dilib)
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