Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes
Identifieur interne : 001267 ( Istex/Corpus ); précédent : 001266; suivant : 001268Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes
Auteurs : Vincent Diemer ; Manon Begaud ; Frédéric R. Leroux ; Françoise ColobertSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2011-01.
English descriptors
- KwdEn :
- Anhydrous, Aryllithium, Aryllithiums, Aryne, Aryne reaction, Arynes, Begaud, Benzyne, Biaryl, Biaryls, Butyllithium, Butyllithium mmol, Cdcl3, Chem, Colobert, Column chromatography, Crude product, Diemer, Dropwise, Electronic effects, Et2o, Functionalized, Gmbh, Hexane, Kgaa, Larock, Leroux, Lett, Meoh, Meta, Methoxy group, Methyl group, Mmol, Och3, Organic layer, Organic layers, Ortho, Ortho position, Precursor, Reaction mixture, Regioisomer, Regioselectivity, Spectroscopic data, Steric, Steric hindrance, Substituents, Verlag, Verlag gmbh, Weinheim.
- Teeft :
- Anhydrous, Aryllithium, Aryllithiums, Aryne, Aryne reaction, Arynes, Begaud, Benzyne, Biaryl, Biaryls, Butyllithium, Butyllithium mmol, Cdcl3, Chem, Colobert, Column chromatography, Crude product, Diemer, Dropwise, Electronic effects, Et2o, Functionalized, Gmbh, Hexane, Kgaa, Larock, Leroux, Lett, Meoh, Meta, Methoxy group, Methyl group, Mmol, Och3, Organic layer, Organic layers, Ortho, Ortho position, Precursor, Reaction mixture, Regioisomer, Regioselectivity, Spectroscopic data, Steric, Steric hindrance, Substituents, Verlag, Verlag gmbh, Weinheim.
Abstract
Tri‐ and tetrasubstituted ortho‐bromobiaryls have been synthesized in good‐to‐excellent yields by aryne cross‐coupling reactions starting from 1,3‐dimethoxybenzene and functionalized 1,2‐dibromobenzenes. This study outlines the influence of the 1,2‐dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl–aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross‐coupling reactions.
Url:
DOI: 10.1002/ejoc.201001283
Links to Exploration step
ISTEX:974AF474597A0E575B2835BF5ADF1C932F12912ELe document en format XML
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This study outlines the influence of the 1,2‐dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl–aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross‐coupling reactions.</abstract><qualityIndicators><score>5.828</score><pdfVersion>1.3</pdfVersion><pdfPageSize>592.78 x 793.94 pts</pdfPageSize><refBibsNative>true</refBibsNative><abstractCharCount>573</abstractCharCount><pdfWordCount>8157</pdfWordCount><pdfCharCount>44872</pdfCharCount><pdfPageCount>14</pdfPageCount><abstractWordCount>69</abstractWordCount></qualityIndicators><title>Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title><genre><json:string>book-reviews</json:string></genre><host><title>European Journal of Organic Chemistry</title><language><json:string>unknown</json:string></language><doi><json:string>10.1002/(ISSN)1099-0690</json:string></doi><issn><json:string>1434-193X</json:string></issn><eissn><json:string>1099-0690</json:string></eissn><publisherId><json:string>EJOC</json:string></publisherId><volume>2011</volume><issue>2</issue><pages><first>341</first><last>354</last><total>14</total></pages><genre><json:string>journal</json:string></genre><subject><json:item><value>Full Paper</value></json:item></subject></host><categories><wos><json:string>science</json:string><json:string>chemistry, organic</json:string></wos><scienceMetrix><json:string>natural sciences</json:string><json:string>chemistry</json:string><json:string>organic chemistry</json:string></scienceMetrix><inist><json:string>sciences appliquees, technologies et medecines</json:string><json:string>sciences biologiques et medicales</json:string><json:string>sciences biologiques fondamentales et appliquees. psychologie</json:string><json:string>biochimie analytique, structurale et metabolique</json:string></inist></categories><publicationDate>2011</publicationDate><copyrightDate>2011</copyrightDate><doi><json:string>10.1002/ejoc.201001283</json:string></doi><id>974AF474597A0E575B2835BF5ADF1C932F12912E</id><score>1</score><fulltext><json:item><extension>pdf</extension><original>true</original><mimetype>application/pdf</mimetype><uri>https://api.istex.fr/document/974AF474597A0E575B2835BF5ADF1C932F12912E/fulltext/pdf</uri></json:item><json:item><extension>zip</extension><original>false</original><mimetype>application/zip</mimetype><uri>https://api.istex.fr/document/974AF474597A0E575B2835BF5ADF1C932F12912E/fulltext/zip</uri></json:item><istex:fulltextTEI uri="https://api.istex.fr/document/974AF474597A0E575B2835BF5ADF1C932F12912E/fulltext/tei"><teiHeader><fileDesc><titleStmt><title level="a" type="main" xml:lang="en">Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title></titleStmt><publicationStmt><authority>ISTEX</authority><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><availability><licence>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</licence></availability><date type="published" when="2011-01"></date></publicationStmt><notesStmt><note type="content-type" subtype="book-reviews" source="bookReview" scheme="https://content-type.data.istex.fr/ark:/67375/XTP-PBH5VBM9-4">book-reviews</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="book-reviews"><analytic><title level="a" type="main" xml:lang="en">Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title><title level="a" type="short" xml:lang="en">Aryne Cross‐Coupling of Aryllithiums with Dibromobenzenes</title><author xml:id="author-0000"><persName><forename type="first">Vincent</forename><surname>Diemer</surname></persName><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742<address><country key="FR"></country></address></affiliation></author><author xml:id="author-0001"><persName><forename type="first">Manon</forename><surname>Begaud</surname></persName><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742<address><country key="FR"></country></address></affiliation></author><author xml:id="author-0002"><persName><forename type="first">Frédéric R.</forename><surname>Leroux</surname></persName><email>frederic.leroux@unistra.fr</email><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742<address><country key="FR"></country></address></affiliation></author><author xml:id="author-0003"><persName><forename type="first">Françoise</forename><surname>Colobert</surname></persName><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742<address><country key="FR"></country></address></affiliation></author><idno type="istex">974AF474597A0E575B2835BF5ADF1C932F12912E</idno><idno type="ark">ark:/67375/WNG-ZHM1FK68-F</idno><idno type="DOI">10.1002/ejoc.201001283</idno><idno type="unit">EJOC201001283</idno><idno type="toTypesetVersion">file:EJOC.EJOC201001283.pdf</idno></analytic><monogr><title level="j" type="main">European Journal of Organic Chemistry</title><title level="j" type="alt">EUROPEAN JOURNAL OF ORGANIC CHEMISTRY</title><idno type="pISSN">1434-193X</idno><idno type="eISSN">1099-0690</idno><idno type="book-DOI">10.1002/(ISSN)1099-0690</idno><idno type="book-part-DOI">10.1002/ejoc.v2011.2</idno><idno type="product">EJOC</idno><imprint><biblScope unit="vol">2011</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="341">341</biblScope><biblScope unit="page" to="354">354</biblScope><biblScope unit="page-count">14</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2011-01"></date></imprint></monogr></biblStruct></sourceDesc></fileDesc><profileDesc><abstract xml:lang="en" style="main"><head>Abstract</head><p>Tri‐ and tetrasubstituted <hi rend="italic">ortho</hi>‐bromobiaryls have been synthesized in good‐to‐excellent yields by aryne cross‐coupling reactions starting from 1,3‐dimethoxybenzene and functionalized 1,2‐dibromobenzenes. This study outlines the influence of the 1,2‐dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl–aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross‐coupling reactions.</p></abstract><abstract xml:lang="en" style="graphical"><p>A wide range of <hi rend="italic">o</hi>,<hi rend="italic">o</hi>′‐tri‐ and ‐tetrasubstituted biphenyls have been prepared by a transition‐metal‐free “aryne” cross‐coupling starting from 2,6‐dimethoxyphenyllithium and various functionalized 1,2‐dibromobenzenes. Mechanistic investigations outline the key parameters that govern both the aryl–aryl bond formation and the regioselectivity of the reaction with dissymmetrical aryne precursors.
<figure type="box"><media mimeType="image" url="urn:x-wiley:1434193X:media:EJOC201001283:fig000"></media><media mimeType="image/gif" url="" rendition="webLoRes"></media><media mimeType="image/jpeg" url="" rendition="webOriginal"></media><media mimeType="image/jpeg" url="" rendition="webHiRes"></media></figure></p></abstract><textClass><keywords xml:lang="en"><term xml:id="kwd1">Arynes</term><term xml:id="kwd2">Cross‐coupling</term><term xml:id="kwd3">Bromine</term><term xml:id="kwd4">Biaryls</term><term xml:id="kwd5">Regioselectivity</term><term xml:id="kwd6">Lithiation</term></keywords><keywords rend="articleCategory"><term>Full Paper</term></keywords><keywords rend="tocHeading1"><term>Full Papers</term></keywords><keywords rend="tocHeading2"><term>Biaryl Synthesis</term></keywords></textClass><langUsage><language ident="en"></language></langUsage></profileDesc></teiHeader></istex:fulltextTEI><json:item><extension>txt</extension><original>false</original><mimetype>text/plain</mimetype><uri>https://api.istex.fr/document/974AF474597A0E575B2835BF5ADF1C932F12912E/fulltext/txt</uri></json:item></fulltext><metadata><istex:metadataXml wicri:clean="Wiley, elements deleted: body"><istex:xmlDeclaration>version="1.0" encoding="UTF-8" standalone="yes"</istex:xmlDeclaration><istex:document><component version="2.0" type="serialArticle" xml:lang="en"><header><publicationMeta level="product"><publisherInfo><publisherName>WILEY‐VCH Verlag</publisherName><publisherLoc>Weinheim</publisherLoc></publisherInfo><doi registered="yes">10.1002/(ISSN)1099-0690</doi><issn type="print">1434-193X</issn><issn type="electronic">1099-0690</issn><idGroup><id type="product" value="EJOC"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="EUROPEAN JOURNAL OF ORGANIC CHEMISTRY">European Journal of Organic Chemistry</title><title type="short">Eur. J. Org. Chem.</title></titleGroup></publicationMeta><publicationMeta level="part" position="20"><doi origin="wiley" registered="yes">10.1002/ejoc.v2011.2</doi><numberingGroup><numbering type="journalVolume" number="2011">2011</numbering><numbering type="journalIssue">2</numbering></numberingGroup><coverDate startDate="2011-01">January 2011</coverDate></publicationMeta><publicationMeta level="unit" type="bookReview" position="20" status="forIssue"><doi origin="wiley" registered="yes">10.1002/ejoc.201001283</doi><idGroup><id type="unit" value="EJOC201001283"></id></idGroup><countGroup><count type="pageTotal" number="14"></count></countGroup><titleGroup><title type="articleCategory">Full Paper</title><title type="tocHeading1">Full Papers</title><title type="tocHeading2">Biaryl Synthesis</title></titleGroup><copyright ownership="publisher">Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2010-09-13"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.4.2 mode:FullText" date="2010-12-29"></event><event type="publishedOnlineEarlyUnpaginated" date="2010-12-02"></event><event type="firstOnline" date="2010-12-02"></event><event type="publishedOnlineFinalForm" date="2010-12-29"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-24"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-16"></event></eventGroup><numberingGroup><numbering type="pageFirst">341</numbering><numbering type="pageLast">354</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC201001283.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="10"></count><count type="tableTotal" number="1"></count><count type="referenceTotal" number="27"></count></countGroup><titleGroup><title type="main" xml:lang="en">Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title><title type="short" xml:lang="en">Aryne Cross‐Coupling of Aryllithiums with Dibromobenzenes</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Vincent</givenNames><familyName>Diemer</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Manon</givenNames><familyName>Begaud</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Frédéric R.</givenNames><familyName>Leroux</familyName></personName><contactDetails><email>frederic.leroux@unistra.fr</email></contactDetails></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#af1"><personName><givenNames>Françoise</givenNames><familyName>Colobert</familyName></personName></creator></creators><affiliationGroup><affiliation xml:id="af1" countryCode="FR" type="organization"><unparsedAffiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1">Arynes</keyword><keyword xml:id="kwd2">Cross‐coupling</keyword><keyword xml:id="kwd3">Bromine</keyword><keyword xml:id="kwd4">Biaryls</keyword><keyword xml:id="kwd5">Regioselectivity</keyword><keyword xml:id="kwd6">Lithiation</keyword></keywordGroup><fundingInfo><fundingAgency>Centre National de la Recherche Scientifique (CNRS)</fundingAgency></fundingInfo><fundingInfo><fundingAgency>Ministère de l'Education Nationale et de la Recherche</fundingAgency></fundingInfo><fundingInfo><fundingAgency>Agence Nationale pour la Recherche</fundingAgency><fundingNumber>07‐BLAN‐0292‐01</fundingNumber></fundingInfo><supportingInformation><p>Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer‐reviewed, but not copy‐edited or typeset. They are made available as submitted by the authors.
</p><supportingInfoItem><mediaResource alt="supporting information" href="urn-x:wiley:1434193X:media:ejoc201001283:ejoc_201001283_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>Tri‐ and tetrasubstituted <i>ortho</i>‐bromobiaryls have been synthesized in good‐to‐excellent yields by aryne cross‐coupling reactions starting from 1,3‐dimethoxybenzene and functionalized 1,2‐dibromobenzenes. This study outlines the influence of the 1,2‐dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl–aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross‐coupling reactions.</p></abstract><abstract type="graphical" xml:lang="en"><p>A wide range of <i>o</i>,<i>o</i>′‐tri‐ and ‐tetrasubstituted biphenyls have been prepared by a transition‐metal‐free “aryne” cross‐coupling starting from 2,6‐dimethoxyphenyllithium and various functionalized 1,2‐dibromobenzenes. Mechanistic investigations outline the key parameters that govern both the aryl–aryl bond formation and the regioselectivity of the reaction with dissymmetrical aryne precursors.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:1434193X:media:EJOC201001283:fig000"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/jpeg" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/jpeg" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Aryne Cross‐Coupling of Aryllithiums with Dibromobenzenes</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Regioselectivity in the Aryne Cross‐Coupling of Aryllithiums with Functionalized 1,2‐Dibromobenzenes</title></titleInfo><name type="personal"><namePart type="given">Vincent</namePart><namePart type="family">Diemer</namePart><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Manon</namePart><namePart type="family">Begaud</namePart><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Frédéric R.</namePart><namePart type="family">Leroux</namePart><affiliation>E-mail: frederic.leroux@unistra.fr</affiliation><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</affiliation><affiliation>E-mail: frederic.leroux@unistra.fr</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Françoise</namePart><namePart type="family">Colobert</namePart><affiliation>CNRS et Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="book-reviews" displayLabel="bookReview" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-PBH5VBM9-4">book-reviews</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2011-01</dateIssued><dateCaptured encoding="w3cdtf">2010-09-13</dateCaptured><copyrightDate encoding="w3cdtf">2011</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">10</extent><extent unit="tables">1</extent><extent unit="references">27</extent></physicalDescription><abstract lang="en">Tri‐ and tetrasubstituted ortho‐bromobiaryls have been synthesized in good‐to‐excellent yields by aryne cross‐coupling reactions starting from 1,3‐dimethoxybenzene and functionalized 1,2‐dibromobenzenes. This study outlines the influence of the 1,2‐dibromobenzene precursor as well as the reaction temperature on the outcome of the aryl–aryl bond formation and indicates, in the case of dissymmetrical benzyne precursors, how structural parameters (electronic effects, steric hindrance, temperature, etc.) control the regioselectivity of the aryne cross‐coupling reactions.</abstract><abstract type="graphical" lang="en">A wide range of o,o′‐tri‐ and ‐tetrasubstituted biphenyls have been prepared by a transition‐metal‐free “aryne” cross‐coupling starting from 2,6‐dimethoxyphenyllithium and various functionalized 1,2‐dibromobenzenes. Mechanistic investigations outline the key parameters that govern both the aryl–aryl bond formation and the regioselectivity of the reaction with dissymmetrical aryne precursors.</abstract><note type="funding">Centre National de la Recherche Scientifique (CNRS)</note><note type="funding">Ministère de l'Education Nationale et de la Recherche</note><note type="funding">Agence Nationale pour la Recherche - No. 07‐BLAN‐0292‐01; </note><subject lang="en"><genre>keywords</genre><topic>Arynes</topic><topic>Cross‐coupling</topic><topic>Bromine</topic><topic>Biaryls</topic><topic>Regioselectivity</topic><topic>Lithiation</topic></subject><relatedItem type="host"><titleInfo><title>European Journal of Organic Chemistry</title></titleInfo><titleInfo type="abbreviated"><title>Eur. J. Org. 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