Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes
Identifieur interne : 000C12 ( Istex/Corpus ); précédent : 000C11; suivant : 000C13Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes
Auteurs : Vincent Diemer ; Frédéric R. Leroux ; Françoise ColobertSource :
- European Journal of Organic Chemistry [ 1434-193X ] ; 2011-01.
English descriptors
- KwdEn :
- Angew, Anhydrous, Aniline, Aryne, Biaryl, Boronic, Boronic ester, Calcd, Cdcl3, Chem, Colobert, Colorless, Column chromatography, Cyclohexane, Diazonium, Diazonium salt, Diemer, Dropwise, Ester, Et2o, Functionalized, Further purification, Gmbh, Hexane, Hrms, Kgaa, Knochel, Larock, Leroux, Lett, Meoh, Metalation, Mmol, Nucleophilic, Och3, Organic layer, Organic layers, Permutation, Precursor, Regioselective, Spectroscopic, Spectroscopic data, Tetrahedron, Tetrahedron lett, Tmscl, Toluene, Verlag, Verlag gmbh, Weinheim.
- Teeft :
- Angew, Anhydrous, Aniline, Aryne, Biaryl, Boronic, Boronic ester, Calcd, Cdcl3, Chem, Colobert, Colorless, Column chromatography, Cyclohexane, Diazonium, Diazonium salt, Diemer, Dropwise, Ester, Et2o, Functionalized, Further purification, Gmbh, Hexane, Hrms, Kgaa, Knochel, Larock, Leroux, Lett, Meoh, Metalation, Mmol, Nucleophilic, Och3, Organic layer, Organic layers, Permutation, Precursor, Regioselective, Spectroscopic, Spectroscopic data, Tetrahedron, Tetrahedron lett, Tmscl, Toluene, Verlag, Verlag gmbh, Weinheim.
Abstract
1,2‐Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, ortho‐metalation, and halogen/metal permutations. 1,2‐Dibromo‐3‐iodobenzene (2f), 1,2‐dibromo‐4‐iodobenzene (4c), and 2,3‐dibromo‐1,4‐diiodobenzene (5e) act as intermediates in these syntheses.
Url:
DOI: 10.1002/ejoc.201001217
Links to Exploration step
ISTEX:00B8AE2CC871EF51AC29C430B984F3C1652C9528Le document en format XML
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Leroux</name><affiliations><json:string>CNRS/Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</json:string><json:string>E-mail: frederic.leroux@unistra.fr</json:string></affiliations></json:item><json:item><name>Françoise Colobert</name><affiliations><json:string>CNRS/Université de Strasbourg (ECPM), UMR CNRS 7509, 25 rue Becquerel, 67087 Strasbourg, France, Fax: +33‐3‐68852742</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>Halogens</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Metalation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Magnesium</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Arynes</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Arenes</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>Cross‐coupling</value></json:item></subject><articleId><json:string>EJOC201001217</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>bookReview</json:string></originalGenre><abstract>Bromo‐iodoarenes have been synthesized by short and regioselective bromination or iodination sequences that combine ortho‐metalation, halo‐desilylation, diazotation, or bromination reactions of anilines. 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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">Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes</title><title level="a" type="short" xml:lang="en">Synthesis of 1,2‐Dibromobenzenes</title><author xml:id="author-0000"><persName><forename type="first">Vincent</forename><surname>Diemer</surname></persName><affiliation>CNRS/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">Frédéric R.</forename><surname>Leroux</surname></persName><email>frederic.leroux@unistra.fr</email><affiliation>CNRS/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">Françoise</forename><surname>Colobert</surname></persName><affiliation>CNRS/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">00B8AE2CC871EF51AC29C430B984F3C1652C9528</idno><idno type="ark">ark:/67375/WNG-BB1KR27G-W</idno><idno type="DOI">10.1002/ejoc.201001217</idno><idno type="unit">EJOC201001217</idno><idno type="toTypesetVersion">file:EJOC.EJOC201001217.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="327">327</biblScope><biblScope unit="page" to="340">340</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>1,2‐Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, <hi rend="italic">ortho</hi>‐metalation, and halogen/metal permutations. 1,2‐Dibromo‐3‐iodobenzene (<hi rend="bold">2f</hi>), 1,2‐dibromo‐4‐iodobenzene (<hi rend="bold">4c</hi>), and 2,3‐dibromo‐1,4‐diiodobenzene (<hi rend="bold">5e</hi>) act as intermediates in these syntheses.</p></abstract><abstract xml:lang="en" style="graphical"><p>Bromo‐iodoarenes have been synthesized by short and regioselective bromination or iodination sequences that combine <hi rend="italic">ortho</hi>‐metalation, halo‐desilylation, diazotation, or bromination reactions of anilines. These polyhalo derivatives were then used as key intermediates to access a wide range of functionalized 1,2‐dibromobenzenes by chemoselective organometallic reactions.
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KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2010-08-27"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.4.2 mode:FullText" date="2010-12-29"></event><event type="publishedOnlineEarlyUnpaginated" date="2010-11-29"></event><event type="firstOnline" date="2010-11-29"></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">327</numbering><numbering type="pageLast">340</numbering></numberingGroup><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:EJOC.EJOC201001217.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="1"></count><count type="tableTotal" number="0"></count><count type="referenceTotal" number="35"></count></countGroup><titleGroup><title type="main" xml:lang="en">Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes</title><title type="short" xml:lang="en">Synthesis of 1,2‐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>Frédéric R.</givenNames><familyName>Leroux</familyName></personName><contactDetails><email>frederic.leroux@unistra.fr</email></contactDetails></creator><creator xml:id="au3" 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/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">Halogens</keyword><keyword xml:id="kwd2">Metalation</keyword><keyword xml:id="kwd3">Magnesium</keyword><keyword xml:id="kwd4">Arynes</keyword><keyword xml:id="kwd5">Arenes</keyword><keyword xml:id="kwd6">Cross‐coupling</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:ejoc201001217:ejoc_201001217_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>1,2‐Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, <i>ortho</i>‐metalation, and halogen/metal permutations. 1,2‐Dibromo‐3‐iodobenzene (<b>2f</b>), 1,2‐dibromo‐4‐iodobenzene (<b>4c</b>), and 2,3‐dibromo‐1,4‐diiodobenzene (<b>5e</b>) act as intermediates in these syntheses.</p></abstract><abstract type="graphical" xml:lang="en"><p>Bromo‐iodoarenes have been synthesized by short and regioselective bromination or iodination sequences that combine <i>ortho</i>‐metalation, halo‐desilylation, diazotation, or bromination reactions of anilines. These polyhalo derivatives were then used as key intermediates to access a wide range of functionalized 1,2‐dibromobenzenes by chemoselective organometallic reactions.
<blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:1434193X:media:EJOC201001217: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>Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes</title></titleInfo><titleInfo type="abbreviated" lang="en"><title>Synthesis of 1,2‐Dibromobenzenes</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2‐Dibromobenzenes</title></titleInfo><name type="personal"><namePart type="given">Vincent</namePart><namePart type="family">Diemer</namePart><affiliation>CNRS/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/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/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">2010-08-27</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">1</extent><extent unit="tables">0</extent><extent unit="references">35</extent></physicalDescription><abstract>1,2‐Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, ortho‐metalation, and halogen/metal permutations. 1,2‐Dibromo‐3‐iodobenzene (2f), 1,2‐dibromo‐4‐iodobenzene (4c), and 2,3‐dibromo‐1,4‐diiodobenzene (5e) act as intermediates in these syntheses.</abstract><abstract type="graphical" lang="en">Bromo‐iodoarenes have been synthesized by short and regioselective bromination or iodination sequences that combine ortho‐metalation, halo‐desilylation, diazotation, or bromination reactions of anilines. These polyhalo derivatives were then used as key intermediates to access a wide range of functionalized 1,2‐dibromobenzenes by chemoselective organometallic reactions.</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>Halogens</topic><topic>Metalation</topic><topic>Magnesium</topic><topic>Arynes</topic><topic>Arenes</topic><topic>Cross‐coupling</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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