Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes
Identifieur interne : 000034 ( Istex/Checkpoint ); précédent : 000033; suivant : 000035Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes
Auteurs : Krzysztof Durka [Pologne] ; Krzysztof Gontarczyk [Pologne] ; Tomasz Kli [Pologne] ; Janusz Serwatowski [Pologne] ; Krzysztof Wo Niak [Pologne]Source :
- Applied Organometallic Chemistry [ 0268-2605 ] ; 2012-06.
Descripteurs français
- Wicri :
- topic : Droit d'auteur.
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
Affiliations:
Links toward previous steps (curation, corpus...)
Links to Exploration step
ISTEX:F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5Le document en format XML
<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes</title><author><name sortKey="Durka, Krzysztof" sort="Durka, Krzysztof" uniqKey="Durka K" first="Krzysztof" last="Durka">Krzysztof Durka</name></author><author><name sortKey="Gontarczyk, Krzysztof" sort="Gontarczyk, Krzysztof" uniqKey="Gontarczyk K" first="Krzysztof" last="Gontarczyk">Krzysztof Gontarczyk</name></author><author><name sortKey="Kli, Tomasz" sort="Kli, Tomasz" uniqKey="Kli T" first="Tomasz" last="Kli">Tomasz Kli</name></author><author><name sortKey="Serwatowski, Janusz" sort="Serwatowski, Janusz" uniqKey="Serwatowski J" first="Janusz" last="Serwatowski">Janusz Serwatowski</name></author><author><name sortKey="Wo Niak, Krzysztof" sort="Wo Niak, Krzysztof" uniqKey="Wo Niak K" first="Krzysztof" last="Wo Niak">Krzysztof Wo Niak</name></author></titleStmt><publicationStmt><idno type="wicri:source">ISTEX</idno><idno type="RBID">ISTEX:F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5</idno><date when="2012" year="2012">2012</date><idno type="doi">10.1002/aoc.2856</idno><idno type="url">https://api.istex.fr/document/F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5/fulltext/pdf</idno><idno type="wicri:Area/Istex/Corpus">001722</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Corpus" wicri:corpus="ISTEX">001722</idno><idno type="wicri:Area/Istex/Curation">001722</idno><idno type="wicri:Area/Istex/Checkpoint">000034</idno><idno type="wicri:explorRef" wicri:stream="Istex" wicri:step="Checkpoint">000034</idno></publicationStmt><sourceDesc><biblStruct><analytic><title level="a" type="main">Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes</title><author><name sortKey="Durka, Krzysztof" sort="Durka, Krzysztof" uniqKey="Durka K" first="Krzysztof" last="Durka">Krzysztof Durka</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw</wicri:regionArea><wicri:noRegion>Warsaw</wicri:noRegion></affiliation></author><author><name sortKey="Gontarczyk, Krzysztof" sort="Gontarczyk, Krzysztof" uniqKey="Gontarczyk K" first="Krzysztof" last="Gontarczyk">Krzysztof Gontarczyk</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw</wicri:regionArea><wicri:noRegion>Warsaw</wicri:noRegion></affiliation></author><author><name sortKey="Kli, Tomasz" sort="Kli, Tomasz" uniqKey="Kli T" first="Tomasz" last="Kli">Tomasz Kli</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw</wicri:regionArea><wicri:noRegion>Warsaw</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Pologne</country></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Pologne</country></affiliation></author><author><name sortKey="Serwatowski, Janusz" sort="Serwatowski, Janusz" uniqKey="Serwatowski J" first="Janusz" last="Serwatowski">Janusz Serwatowski</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Chemistry, Warsaw University of Technology, 00‐664, Warsaw</wicri:regionArea><wicri:noRegion>Warsaw</wicri:noRegion></affiliation></author><author><name sortKey="Wo Niak, Krzysztof" sort="Wo Niak, Krzysztof" uniqKey="Wo Niak K" first="Krzysztof" last="Wo Niak">Krzysztof Wo Niak</name><affiliation wicri:level="1"><country xml:lang="fr">Pologne</country><wicri:regionArea>Faculty of Chemistry, Warsaw University, 02‐093, Warsaw</wicri:regionArea><wicri:noRegion>Warsaw</wicri:noRegion></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Applied Organometallic Chemistry</title><title level="j" type="alt">APPLIED ORGANOMETALLIC CHEMISTRY</title><idno type="ISSN">0268-2605</idno><idno type="eISSN">1099-0739</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">2012-06</date></imprint><idno type="ISSN">0268-2605</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0268-2605</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Acta cryst</term><term>Anal</term><term>Appl</term><term>Aryllithiums</term><term>Benzylic</term><term>Benzylic hydrogen</term><term>Benzylic position</term><term>Boronic</term><term>Boronic acid</term><term>Boronic acids</term><term>Calcd</term><term>Cbenz</term><term>Cdcl3</term><term>Chem</term><term>Copyright</term><term>Cyano</term><term>Cyano group</term><term>Deprotonation</term><term>Equiv</term><term>John wiley sons</term><term>Lithiation</term><term>Me3sicl</term><term>Oxygen atoms</term><term>Phenyl ring</term><term>Reaction conditions</term><term>Uorine</term><term>Uorine atoms</term><term>Warsaw university</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Acta cryst</term><term>Anal</term><term>Appl</term><term>Aryllithiums</term><term>Benzylic</term><term>Benzylic hydrogen</term><term>Benzylic position</term><term>Boronic</term><term>Boronic acid</term><term>Boronic acids</term><term>Calcd</term><term>Cbenz</term><term>Cdcl3</term><term>Chem</term><term>Copyright</term><term>Cyano</term><term>Cyano group</term><term>Deprotonation</term><term>Equiv</term><term>John wiley sons</term><term>Lithiation</term><term>Me3sicl</term><term>Oxygen atoms</term><term>Phenyl ring</term><term>Reaction conditions</term><term>Uorine</term><term>Uorine atoms</term><term>Warsaw university</term></keywords><keywords scheme="Wicri" type="topic" xml:lang="fr"><term>Droit d'auteur</term></keywords></textClass></profileDesc></teiHeader><front><div type="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.</div></front></TEI><affiliations><list><country><li>Pologne</li></country></list><tree><country name="Pologne"><noRegion><name sortKey="Durka, Krzysztof" sort="Durka, Krzysztof" uniqKey="Durka K" first="Krzysztof" last="Durka">Krzysztof Durka</name></noRegion><name sortKey="Gontarczyk, Krzysztof" sort="Gontarczyk, Krzysztof" uniqKey="Gontarczyk K" first="Krzysztof" last="Gontarczyk">Krzysztof Gontarczyk</name><name sortKey="Kli, Tomasz" sort="Kli, Tomasz" uniqKey="Kli T" first="Tomasz" last="Kli">Tomasz Kli</name><name sortKey="Kli, Tomasz" sort="Kli, Tomasz" uniqKey="Kli T" first="Tomasz" last="Kli">Tomasz Kli</name><name sortKey="Kli, Tomasz" sort="Kli, Tomasz" uniqKey="Kli T" first="Tomasz" last="Kli">Tomasz Kli</name><name sortKey="Serwatowski, Janusz" sort="Serwatowski, Janusz" uniqKey="Serwatowski J" first="Janusz" last="Serwatowski">Janusz Serwatowski</name><name sortKey="Wo Niak, Krzysztof" sort="Wo Niak, Krzysztof" uniqKey="Wo Niak K" first="Krzysztof" last="Wo Niak">Krzysztof Wo Niak</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/Lorraine/explor/LrgpV1/Data/Istex/Checkpoint
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000034 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Istex/Checkpoint/biblio.hfd -nk 000034 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Wicri/Lorraine
|area= LrgpV1
|flux= Istex
|étape= Checkpoint
|type= RBID
|clé= ISTEX:F5E4AE2B372A16DBD5739869B9B7635C8D29BDF5
|texte= Stability of some aryllithiums in the presence of cyano group: synthesis of biaromatic cyanoarylboronic acids and silanes
}}
| This area was generated with Dilib version V0.6.32. |  |