A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates
Identifieur interne : 001223 ( Main/Exploration ); précédent : 001222; suivant : 001224A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates
Auteurs : Frédéric Leroux [France] ; Laurence Bonnafoux [France] ; Christophe Heiss [France] ; Françoise Colobert [France] ; Don Antoine Lanfranchi [France]Source :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2007-12-10.
Descripteurs français
- Wicri :
- topic : éthanol.
English descriptors
- KwdEn :
- Aqueous solution, Aryllithium, Aryne, Aryne source, Biaryl, Biaryls, Biphenyl, Butyllithium, Catal, Chem, Chlorodicyclohexylphosphine, Colorless, Colorless cubes, Colorless needles, Column chromatography, Cyclohexane, Diethyl, Diethyl ether, Diphosphine ligands, Eluent, Ethanol, Ether, Gmbh, Hexane, Hours period, Kgaa, Leroux, Ligand, Mmol, Organic layers, Practical transition, Reaction mixture, Room temperature, Schlosser, Silica, Sodium sulfate, Sulfate, Synth, Tetrahydrofuran, Trisubstituted biaryls, Update, Updates scheme, Verlag, Verlag gmbh, Weinheim.
- Teeft :
- Aqueous solution, Aryllithium, Aryne, Aryne source, Biaryl, Biaryls, Biphenyl, Butyllithium, Catal, Chem, Chlorodicyclohexylphosphine, Colorless, Colorless cubes, Colorless needles, Column chromatography, Cyclohexane, Diethyl, Diethyl ether, Diphosphine ligands, Eluent, Ethanol, Ether, Gmbh, Hexane, Hours period, Kgaa, Leroux, Ligand, Mmol, Organic layers, Practical transition, Reaction mixture, Room temperature, Schlosser, Silica, Sodium sulfate, Sulfate, Synth, Tetrahydrofuran, Trisubstituted biaryls, Update, Updates scheme, Verlag, Verlag gmbh, Weinheim.
Abstract
Upon treatment of various aryllithium intermediates with 1,2‐dibromobenzene or 1‐bromo‐2‐iodobenzene, dissymmetrical ortho,ortho′‐di‐, tri‐ and even tetrasubstituted bromo‐ or iodobiaryls become readily available. The crucial steps in all these reactions were the nucleophilic addition of the organolithium precursor to a transient aryne species released from it by β‐elimination of a lithium halide and, stabilization of the resulting 2‐biaryllithium intermediate by in situ transfer of bromine or iodine from the starting material. This straightforward transition metal‐free access to biaryls allows the preparation of highly valuable halobiaryls on a gram scale in excellent yields. These precursors can be subsequently functionalized by highly regioselective halogen/metal permutations into a vast variety of target molecules. This was demonstrated in the synthesis of several mono‐ and diphosphine ligands.
Url:
DOI: 10.1002/adsc.200700211
Affiliations:
- France
- Alsace (région administrative), Grand Est
- Strasbourg
- Université Strasbourg 1, Université de Strasbourg
Links toward previous steps (curation, corpus...)
- to stream Istex, to step Corpus: 001723
- to stream Istex, to step Curation: 001723
- to stream Istex, to step Checkpoint: 000278
- to stream Main, to step Merge: 001433
- to stream Main, to step Curation: 001223
Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates</title>
<author><name sortKey="Leroux, Frederic" sort="Leroux, Frederic" uniqKey="Leroux F" first="Frédéric" last="Leroux">Frédéric Leroux</name>
</author>
<author><name sortKey="Bonnafoux, Laurence" sort="Bonnafoux, Laurence" uniqKey="Bonnafoux L" first="Laurence" last="Bonnafoux">Laurence Bonnafoux</name>
</author>
<author><name sortKey="Heiss, Christophe" sort="Heiss, Christophe" uniqKey="Heiss C" first="Christophe" last="Heiss">Christophe Heiss</name>
</author>
<author><name sortKey="Colobert, Francoise" sort="Colobert, Francoise" uniqKey="Colobert F" first="Françoise" last="Colobert">Françoise Colobert</name>
</author>
<author><name sortKey="Lanfranchi, Don Antoine" sort="Lanfranchi, Don Antoine" uniqKey="Lanfranchi D" first="Don Antoine" last="Lanfranchi">Don Antoine Lanfranchi</name>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">ISTEX</idno>
<idno type="RBID">ISTEX:252E46DC67C2FC99E026E4362FC0A53AA2FD6591</idno>
<date when="2007" year="2007">2007</date>
<idno type="doi">10.1002/adsc.200700211</idno>
<idno type="url">https://api.istex.fr/document/252E46DC67C2FC99E026E4362FC0A53AA2FD6591/fulltext/pdf</idno>
<idno type="wicri:Area/Istex/Corpus">001723</idno>
<idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">001723</idno>
<idno type="wicri:Area/Istex/Curation">001723</idno>
<idno type="wicri:Area/Istex/Checkpoint">000278</idno>
<idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000278</idno>
<idno type="wicri:doubleKey">1615-4150:2007:Leroux F:a:practical:transition</idno>
<idno type="wicri:Area/Main/Merge">001433</idno>
<idno type="wicri:Area/Main/Curation">001223</idno>
<idno type="wicri:Area/Main/Exploration">001223</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title level="a" type="main" xml:lang="en">A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates</title>
<author><name sortKey="Leroux, Frederic" sort="Leroux, Frederic" uniqKey="Leroux F" first="Frédéric" last="Leroux">Frédéric Leroux</name>
<affiliation wicri:level="1"><country wicri:rule="url">France</country>
</affiliation>
<affiliation wicri:level="4"><country>France</country>
<placeName><settlement type="city">Strasbourg</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Alsace (région administrative)</region>
</placeName>
<orgName type="university">Université Strasbourg 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université de Strasbourg</orgName>
</affiliation>
<affiliation wicri:level="1"><country wicri:rule="url">France</country>
</affiliation>
</author>
<author><name sortKey="Bonnafoux, Laurence" sort="Bonnafoux, Laurence" uniqKey="Bonnafoux L" first="Laurence" last="Bonnafoux">Laurence Bonnafoux</name>
<affiliation wicri:level="4"><country>France</country>
<placeName><settlement type="city">Strasbourg</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Alsace (région administrative)</region>
</placeName>
<orgName type="university">Université Strasbourg 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université de Strasbourg</orgName>
</affiliation>
</author>
<author><name sortKey="Heiss, Christophe" sort="Heiss, Christophe" uniqKey="Heiss C" first="Christophe" last="Heiss">Christophe Heiss</name>
<affiliation wicri:level="4"><country>France</country>
<placeName><settlement type="city">Strasbourg</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Alsace (région administrative)</region>
</placeName>
<orgName type="university">Université Strasbourg 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université de Strasbourg</orgName>
</affiliation>
</author>
<author><name sortKey="Colobert, Francoise" sort="Colobert, Francoise" uniqKey="Colobert F" first="Françoise" last="Colobert">Françoise Colobert</name>
<affiliation wicri:level="4"><country>France</country>
<placeName><settlement type="city">Strasbourg</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Alsace (région administrative)</region>
</placeName>
<orgName type="university">Université Strasbourg 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université de Strasbourg</orgName>
</affiliation>
</author>
<author><name sortKey="Lanfranchi, Don Antoine" sort="Lanfranchi, Don Antoine" uniqKey="Lanfranchi D" first="Don Antoine" last="Lanfranchi">Don Antoine Lanfranchi</name>
<affiliation wicri:level="4"><country>France</country>
<placeName><settlement type="city">Strasbourg</settlement>
<region type="region" nuts="2">Grand Est</region>
<region type="old region" nuts="2">Alsace (région administrative)</region>
</placeName>
<orgName type="university">Université Strasbourg 1</orgName>
<orgName type="institution" wicri:auto="newGroup">Université de Strasbourg</orgName>
</affiliation>
</author>
</analytic>
<monogr></monogr>
<series><title level="j" type="main">Advanced Synthesis & Catalysis</title>
<title level="j" type="sub">Dedicated Cluster</title>
<title level="j" type="alt">ADVANCED SYNTHESIS CATALYSIS</title>
<idno type="ISSN">1615-4150</idno>
<idno type="eISSN">1615-4169</idno>
<imprint><biblScope unit="vol">349</biblScope>
<biblScope unit="issue">17‐18</biblScope>
<biblScope unit="page" from="2705">2705</biblScope>
<biblScope unit="page" to="2713">2713</biblScope>
<biblScope unit="page-count">9</biblScope>
<publisher>WILEY‐VCH Verlag</publisher>
<pubPlace>Weinheim</pubPlace>
<date type="published" when="2007-12-10">2007-12-10</date>
</imprint>
<idno type="ISSN">1615-4150</idno>
</series>
</biblStruct>
</sourceDesc>
<seriesStmt><idno type="ISSN">1615-4150</idno>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aqueous solution</term>
<term>Aryllithium</term>
<term>Aryne</term>
<term>Aryne source</term>
<term>Biaryl</term>
<term>Biaryls</term>
<term>Biphenyl</term>
<term>Butyllithium</term>
<term>Catal</term>
<term>Chem</term>
<term>Chlorodicyclohexylphosphine</term>
<term>Colorless</term>
<term>Colorless cubes</term>
<term>Colorless needles</term>
<term>Column chromatography</term>
<term>Cyclohexane</term>
<term>Diethyl</term>
<term>Diethyl ether</term>
<term>Diphosphine ligands</term>
<term>Eluent</term>
<term>Ethanol</term>
<term>Ether</term>
<term>Gmbh</term>
<term>Hexane</term>
<term>Hours period</term>
<term>Kgaa</term>
<term>Leroux</term>
<term>Ligand</term>
<term>Mmol</term>
<term>Organic layers</term>
<term>Practical transition</term>
<term>Reaction mixture</term>
<term>Room temperature</term>
<term>Schlosser</term>
<term>Silica</term>
<term>Sodium sulfate</term>
<term>Sulfate</term>
<term>Synth</term>
<term>Tetrahydrofuran</term>
<term>Trisubstituted biaryls</term>
<term>Update</term>
<term>Updates scheme</term>
<term>Verlag</term>
<term>Verlag gmbh</term>
<term>Weinheim</term>
</keywords>
<keywords scheme="Teeft" xml:lang="en"><term>Aqueous solution</term>
<term>Aryllithium</term>
<term>Aryne</term>
<term>Aryne source</term>
<term>Biaryl</term>
<term>Biaryls</term>
<term>Biphenyl</term>
<term>Butyllithium</term>
<term>Catal</term>
<term>Chem</term>
<term>Chlorodicyclohexylphosphine</term>
<term>Colorless</term>
<term>Colorless cubes</term>
<term>Colorless needles</term>
<term>Column chromatography</term>
<term>Cyclohexane</term>
<term>Diethyl</term>
<term>Diethyl ether</term>
<term>Diphosphine ligands</term>
<term>Eluent</term>
<term>Ethanol</term>
<term>Ether</term>
<term>Gmbh</term>
<term>Hexane</term>
<term>Hours period</term>
<term>Kgaa</term>
<term>Leroux</term>
<term>Ligand</term>
<term>Mmol</term>
<term>Organic layers</term>
<term>Practical transition</term>
<term>Reaction mixture</term>
<term>Room temperature</term>
<term>Schlosser</term>
<term>Silica</term>
<term>Sodium sulfate</term>
<term>Sulfate</term>
<term>Synth</term>
<term>Tetrahydrofuran</term>
<term>Trisubstituted biaryls</term>
<term>Update</term>
<term>Updates scheme</term>
<term>Verlag</term>
<term>Verlag gmbh</term>
<term>Weinheim</term>
</keywords>
<keywords scheme="Wicri" type="topic" xml:lang="fr"><term>éthanol</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">Upon treatment of various aryllithium intermediates with 1,2‐dibromobenzene or 1‐bromo‐2‐iodobenzene, dissymmetrical ortho,ortho′‐di‐, tri‐ and even tetrasubstituted bromo‐ or iodobiaryls become readily available. The crucial steps in all these reactions were the nucleophilic addition of the organolithium precursor to a transient aryne species released from it by β‐elimination of a lithium halide and, stabilization of the resulting 2‐biaryllithium intermediate by in situ transfer of bromine or iodine from the starting material. This straightforward transition metal‐free access to biaryls allows the preparation of highly valuable halobiaryls on a gram scale in excellent yields. These precursors can be subsequently functionalized by highly regioselective halogen/metal permutations into a vast variety of target molecules. This was demonstrated in the synthesis of several mono‐ and diphosphine ligands.</div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Alsace (région administrative)</li>
<li>Grand Est</li>
</region>
<settlement><li>Strasbourg</li>
</settlement>
<orgName><li>Université Strasbourg 1</li>
<li>Université de Strasbourg</li>
</orgName>
</list>
<tree><country name="France"><noRegion><name sortKey="Leroux, Frederic" sort="Leroux, Frederic" uniqKey="Leroux F" first="Frédéric" last="Leroux">Frédéric Leroux</name>
</noRegion>
<name sortKey="Bonnafoux, Laurence" sort="Bonnafoux, Laurence" uniqKey="Bonnafoux L" first="Laurence" last="Bonnafoux">Laurence Bonnafoux</name>
<name sortKey="Colobert, Francoise" sort="Colobert, Francoise" uniqKey="Colobert F" first="Françoise" last="Colobert">Françoise Colobert</name>
<name sortKey="Heiss, Christophe" sort="Heiss, Christophe" uniqKey="Heiss C" first="Christophe" last="Heiss">Christophe Heiss</name>
<name sortKey="Lanfranchi, Don Antoine" sort="Lanfranchi, Don Antoine" uniqKey="Lanfranchi D" first="Don Antoine" last="Lanfranchi">Don Antoine Lanfranchi</name>
<name sortKey="Leroux, Frederic" sort="Leroux, Frederic" uniqKey="Leroux F" first="Frédéric" last="Leroux">Frédéric Leroux</name>
<name sortKey="Leroux, Frederic" sort="Leroux, Frederic" uniqKey="Leroux F" first="Frédéric" last="Leroux">Frédéric Leroux</name>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Lorraine/explor/LrgpV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 001223 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 001223 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Wicri/Lorraine |area= LrgpV1 |flux= Main |étape= Exploration |type= RBID |clé= ISTEX:252E46DC67C2FC99E026E4362FC0A53AA2FD6591 |texte= A Practical Transition Metal‐Free Aryl‐Aryl Coupling Method: Arynes as Key Intermediates }}
![]() | This area was generated with Dilib version V0.6.32. | ![]() |