One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
Identifieur interne : 000598 ( Istex/Corpus ); précédent : 000597; suivant : 000599One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System
Auteurs : Alice Devineau ; Guillaume Pousse ; Catherine Taillier ; Jérôme Blanchet ; Jacques Rouden ; Vincent DallaSource :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2010-11-22.
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Abstract
A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.
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DOI: 10.1002/adsc.201000602
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ISTEX:43AFE2A8810F3420B8C3DD48B321E216C2596714Le document en format XML
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The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Alice Devineau</name><affiliations><json:string>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</json:string></affiliations></json:item><json:item><name>Guillaume Pousse</name><affiliations><json:string>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</json:string></affiliations></json:item><json:item><name>Catherine Taillier</name><affiliations><json:string>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</json:string></affiliations></json:item><json:item><name>Jérôme Blanchet</name><affiliations><json:string>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</json:string></affiliations></json:item><json:item><name>Jacques Rouden</name><affiliations><json:string>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</json:string></affiliations></json:item><json:item><name>Vincent Dalla</name><affiliations><json:string>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</json:string></affiliations></json:item></author><subject><json:item><lang><json:string>eng</json:string></lang><value>N‐acyliminium</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>alkylation</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>electrophilic alcohols</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>sequential organocatalysis</value></json:item><json:item><lang><json:string>eng</json:string></lang><value>trichloroacetimidates</value></json:item></subject><articleId><json:string>ADSC201000602</json:string></articleId><language><json:string>eng</json:string></language><originalGenre><json:string>shortCommunication</json:string></originalGenre><abstract>A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. 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The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.</p></abstract><abstract xml:lang="en" style="graphical"><p></p></abstract><textClass xml:lang="en"><keywords scheme="keyword"><list><head>keywords</head><item><term>N‐acyliminium</term></item><item><term>alkylation</term></item><item><term>electrophilic alcohols</term></item><item><term>sequential organocatalysis</term></item><item><term>trichloroacetimidates</term></item></list></keywords></textClass><textClass><keywords scheme="Journal Subject"><list><head>article-category</head><item><term>Communication</term></item></list></keywords></textClass></profileDesc><revisionDesc><change when="2010-07-28">Received</change><change when="2010-11-22">Published</change></revisionDesc></teiHeader></istex:fulltextTEI><json:item><original>false</original><mimetype>text/plain</mimetype><extension>txt</extension><uri>https://api.istex.fr/document/43AFE2A8810F3420B8C3DD48B321E216C2596714/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)1615-4169</doi><issn type="print">1615-4150</issn><issn type="electronic">1615-4169</issn><idGroup><id type="product" value="ADSC"></id></idGroup><titleGroup><title type="main" xml:lang="en" sort="ADVANCED SYNTHESIS CATALYSIS">Advanced Synthesis & Catalysis</title><title type="short">Adv. 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Catal.</title></titleGroup><selfCitationGroup><citation type="ancestor" xml:id="cit1"><journalTitle>Journal für praktische Chemie</journalTitle><accessionId ref="info:x-wiley/issn/14369966">1436-9966</accessionId><pubYear year="2000">2000</pubYear><vol>342</vol><issue>8</issue></citation></selfCitationGroup></publicationMeta><publicationMeta level="part" position="170"><doi origin="wiley" registered="yes">10.1002/adsc.v352.17</doi><numberingGroup><numbering type="journalVolume" number="352">352</numbering><numbering type="journalIssue">17</numbering></numberingGroup><coverDate startDate="2010-11-22">November 22, 2010</coverDate></publicationMeta><publicationMeta level="unit" type="shortCommunication" position="7" status="forIssue"><doi origin="wiley" registered="yes">10.1002/adsc.201000602</doi><idGroup><id type="unit" value="ADSC201000602"></id></idGroup><countGroup><count type="pageTotal" number="6"></count></countGroup><titleGroup><title type="articleCategory">Communication</title><title type="tocHeading1">Communications</title></titleGroup><copyright ownership="publisher">Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</copyright><eventGroup><event type="manuscriptReceived" date="2010-07-28"></event><event type="xmlConverted" agent="Converter:JWSART34_TO_WML3G version:2.3.27 mode:FullText" date="2010-11-19"></event><event type="publishedOnlineEarlyUnpaginated" date="2010-11-09"></event><event type="publishedOnlineFinalForm" date="2010-11-19"></event><event type="firstOnline" date="2010-11-09"></event><event type="xmlConverted" agent="Converter:WILEY_ML3G_TO_WILEY_ML3GV2 version:3.8.8" date="2014-01-01"></event><event type="xmlConverted" agent="Converter:WML3G_To_WML3G version:4.1.7 mode:FullText,remove_FC" date="2014-10-14"></event></eventGroup><numberingGroup><numbering type="pageFirst">2881</numbering><numbering type="pageLast">2886</numbering></numberingGroup><correspondenceTo>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</correspondenceTo><objectNameGroup><objectName elementName="figure">Scheme</objectName></objectNameGroup><linkGroup><link type="toTypesetVersion" href="file:ADSC.ADSC201000602.pdf"></link></linkGroup></publicationMeta><contentMeta><countGroup><count type="figureTotal" number="47"></count><count type="tableTotal" number="4"></count><count type="referenceTotal" number="49"></count></countGroup><titleGroup><title type="main" xml:lang="en">One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System</title></titleGroup><creators><creator xml:id="au1" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Alice</givenNames><familyName>Devineau</familyName></personName></creator><creator xml:id="au2" creatorRole="author" affiliationRef="#ab"><personName><givenNames>Guillaume</givenNames><familyName>Pousse</familyName></personName></creator><creator xml:id="au3" creatorRole="author" affiliationRef="#aa"><personName><givenNames>Catherine</givenNames><familyName>Taillier</familyName></personName></creator><creator xml:id="au4" creatorRole="author" affiliationRef="#ab"><personName><givenNames>Jérôme</givenNames><familyName>Blanchet</familyName></personName></creator><creator xml:id="au5" creatorRole="author" affiliationRef="#ab"><personName><givenNames>Jacques</givenNames><familyName>Rouden</familyName></personName></creator><creator xml:id="au6" creatorRole="author" affiliationRef="#aa" corresponding="yes"><personName><givenNames>Vincent</givenNames><familyName>Dalla</familyName></personName><contactDetails><email normalForm="vincent.dalla@univ-lehavre.fr">vincent.dalla@univ‐lehavre.fr</email></contactDetails></creator></creators><affiliationGroup><affiliation xml:id="aa" countryCode="FR" type="organization"><unparsedAffiliation>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</unparsedAffiliation></affiliation><affiliation xml:id="ab" countryCode="FR" type="organization"><unparsedAffiliation>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</unparsedAffiliation></affiliation></affiliationGroup><keywordGroup xml:lang="en" type="author"><keyword xml:id="kwd1"><i>N</i>‐acyliminium</keyword><keyword xml:id="kwd2">alkylation</keyword><keyword xml:id="kwd3">electrophilic alcohols</keyword><keyword xml:id="kwd4">sequential organocatalysis</keyword><keyword xml:id="kwd5">trichloroacetimidates</keyword></keywordGroup><fundingInfo><fundingAgency>region Haute‐Normandie</fundingAgency></fundingInfo><fundingInfo><fundingAgency>réseau CRUNCH</fundingAgency></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:16154150:media:adsc201000602:adsc_201000602_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf<sub>2</sub>NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.</p></abstract><abstract type="graphical" xml:lang="en"><p><blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" eRights="yes" copyright="WILEY-VCH" href="urn:x-wiley:16154150:media:ADSC201000602:content"></mediaResource><mediaResource alt="thumbnail image" rendition="webLoRes" mimeType="image/gif" href=""></mediaResource><mediaResource alt="original image" rendition="webOriginal" mimeType="image/gif" href=""></mediaResource><mediaResource alt="magnified image" rendition="webHiRes" mimeType="image/gif" href=""></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>One‐Pot Hydroxy Group Activation/Carbon‐Carbon Bond Forming Sequence Using a Brønsted Base/Brønsted Acid System</title></titleInfo><name type="personal"><namePart type="given">Alice</namePart><namePart type="family">Devineau</namePart><affiliation>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Guillaume</namePart><namePart type="family">Pousse</namePart><affiliation>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Catherine</namePart><namePart type="family">Taillier</namePart><affiliation>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jérôme</namePart><namePart type="family">Blanchet</namePart><affiliation>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jacques</namePart><namePart type="family">Rouden</namePart><affiliation>Laboratoire de Chimie Moléculaire et Thio‐organique, ENSICAEN, Université de Caen Basse‐Normandie UMR 6507, CNRS‐INC3 M FR3038; 6 boulevard du Maréchal Juin, 14050 Caen, France</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Vincent</namePart><namePart type="family">Dalla</namePart><affiliation>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</affiliation><affiliation>URCOM, EA 3221, FR3038, Université du Havre, 25 rue Philippe Lebon, BP 540, 76058 Le Havre, France, Fax: (+33)‐2‐3274‐4391; phone: (+33)‐2‐3274‐4401</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="brief-communication" displayLabel="shortCommunication"></genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2010-11-22</dateIssued><dateCaptured encoding="w3cdtf">2010-07-28</dateCaptured><copyrightDate encoding="w3cdtf">2010</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><internetMediaType>text/html</internetMediaType><extent unit="figures">47</extent><extent unit="tables">4</extent><extent unit="references">49</extent></physicalDescription><abstract lang="en">A new sequential two‐step multicatalytic strategy is presented consisting in the efficient DBU‐catalysed trichloroacetimidation of an alcohol followed by a ditriflylamine (Tf2NH)‐catalysed intermolecular alkylation by silicon‐based nucleophiles and CH nucleophiles. The distinct feature of the trichloroacetimidate group allows use of weaker acid catalysts such as 1,1′‐bi‐2‐naphthol (BINOL)‐derived phosphoric acid, pointing out the possible development of an enantioselective variant. This unprecedented sequential one‐pot Brønsted base‐Brønsted acid catalysis further expands the synthetic scope of the trichloroacetimidate group.</abstract><abstract type="graphical" lang="en"></abstract><note type="funding">region Haute‐Normandie</note><note type="funding">réseau CRUNCH</note><subject lang="en"><genre>keywords</genre><topic>N‐acyliminium</topic><topic>alkylation</topic><topic>electrophilic alcohols</topic><topic>sequential organocatalysis</topic><topic>trichloroacetimidates</topic></subject><relatedItem type="host"><titleInfo><title>Advanced Synthesis & Catalysis</title></titleInfo><titleInfo type="abbreviated"><title>Adv. Synth. Catal.</title></titleInfo><genre type="journal">journal</genre><note type="content"> 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.Supporting Info Item: miscellaneous_information - </note><subject><genre>article-category</genre><topic>Communication</topic></subject><identifier type="ISSN">1615-4150</identifier><identifier type="eISSN">1615-4169</identifier><identifier type="DOI">10.1002/(ISSN)1615-4169</identifier><identifier type="PublisherID">ADSC</identifier><part><date>2010</date><detail type="volume"><caption>vol.</caption><number>352</number></detail><detail type="issue"><caption>no.</caption><number>17</number></detail><extent unit="pages"><start>2881</start><end>2886</end><total>6</total></extent></part></relatedItem><relatedItem type="preceding"><titleInfo><title>Journal für praktische Chemie</title></titleInfo><identifier type="ISSN">1436-9966</identifier><part><date point="end">2000</date><detail type="volume"><caption>last vol.</caption><number>342</number></detail><detail type="issue"><caption>last no.</caption><number>8</number></detail></part></relatedItem><identifier type="istex">43AFE2A8810F3420B8C3DD48B321E216C2596714</identifier><identifier type="DOI">10.1002/adsc.201000602</identifier><identifier type="ArticleID">ADSC201000602</identifier><accessCondition type="use and reproduction" contentType="copyright">Copyright © 2010 WILEY‐VCH Verlag GmbH & Co. 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