Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation.
Identifieur interne : 000594 ( Main/Exploration ); précédent : 000593; suivant : 000595Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation.
Auteurs : RBID : pubmed:23219615English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Ketones.
- chemical , chemistry : Hydrocarbons, Chlorinated, Indium, Ketones, Tin Compounds.
- chemical , radiation effects : Ketones, Tin Compounds.
- Catalysis, Molecular Structure, Sonication, Sound.
Abstract
The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.
DOI: 10.1016/j.ultsonch.2012.10.018
PubMed: 23219615
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation.</title><author><name sortKey="Lo Fiego, Marcos J" uniqKey="Lo Fiego M">Marcos J Lo Fiego</name><affiliation wicri:level="1"><nlm:affiliation>Instituto de Química del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca B8000CPB, Argentina.</nlm:affiliation><country xml:lang="fr">Argentine</country><wicri:regionArea>Instituto de Química del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca B8000CPB</wicri:regionArea></affiliation></author><author><name sortKey="Badajoz, Mercedes A" uniqKey="Badajoz M">Mercedes A Badajoz</name></author><author><name sortKey="Domini, Claudia" uniqKey="Domini C">Claudia Domini</name></author><author><name sortKey="Chopa, Alicia B" uniqKey="Chopa A">Alicia B Chopa</name></author><author><name sortKey="Lockhart, Mar A T" uniqKey="Lockhart M">María T Lockhart</name></author></titleStmt><publicationStmt><date when="2013">2013</date><idno type="doi">10.1016/j.ultsonch.2012.10.018</idno><idno type="RBID">pubmed:23219615</idno><idno type="pmid">23219615</idno><idno type="wicri:Area/Main/Corpus">000903</idno><idno type="wicri:Area/Main/Curation">000903</idno><idno type="wicri:Area/Main/Exploration">000594</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Catalysis</term><term>Hydrocarbons, Chlorinated (chemistry)</term><term>Indium (chemistry)</term><term>Ketones (chemical synthesis)</term><term>Ketones (chemistry)</term><term>Ketones (radiation effects)</term><term>Molecular Structure</term><term>Sonication</term><term>Sound</term><term>Tin Compounds (chemistry)</term><term>Tin Compounds (radiation effects)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Ketones</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Hydrocarbons, Chlorinated</term><term>Indium</term><term>Ketones</term><term>Tin Compounds</term></keywords><keywords scheme="MESH" type="chemical" qualifier="radiation effects" xml:lang="en"><term>Ketones</term><term>Tin Compounds</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Molecular Structure</term><term>Sonication</term><term>Sound</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">23219615</PMID><DateCreated><Year>2013</Year><Month>01</Month><Day>21</Day></DateCreated><DateCompleted><Year>2013</Year><Month>07</Month><Day>05</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1873-2828</ISSN><JournalIssue CitedMedium="Internet"><Volume>20</Volume><Issue>3</Issue><PubDate><Year>2013</Year><Month>May</Month></PubDate></JournalIssue><Title>Ultrasonics sonochemistry</Title><ISOAbbreviation>Ultrason Sonochem</ISOAbbreviation></Journal><ArticleTitle>Indium-mediated regioselective synthesis of ketones from arylstannanes under solvent-free ultrasound irradiation.</ArticleTitle><Pagination><MedlinePgn>826-32</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.ultsonch.2012.10.018</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S1350-4177(12)00244-1</ELocationID><Abstract><AbstractText>The solvent-free indium-promoted reaction of alkanoyl chlorides with sterically and electronically diverse arylstannanes is a simple and direct method for the regioselective synthesis of primary, secondary and tertiary alkyl aryl ketones in good to excellent isolated yields (42-84%) under mild and neutral conditions. The protocol is also adequate for the synthesis of aryl vinyl ketones. Reaction times are drastically reduced (from 3-32h to 10-70min) under ultrasonic irradiation. Evidences for the involvement of a homolytic aromatic ipso-substitution mechanism, in which indium metal acts as radical initiator, are presented. It is possible the transference of two aryl groups from tin, thus improving effective mass yield, working with diarylstannanes as starting substrates.</AbstractText><CopyrightInformation>Copyright © 2012 Elsevier B.V. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Lo Fiego</LastName><ForeName>Marcos J</ForeName><Initials>MJ</Initials><Affiliation>Instituto de Química del Sur (CONICET-UNS), Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca B8000CPB, Argentina.</Affiliation></Author><Author ValidYN="Y"><LastName>Badajoz</LastName><ForeName>Mercedes A</ForeName><Initials>MA</Initials></Author><Author ValidYN="Y"><LastName>Domini</LastName><ForeName>Claudia</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Chopa</LastName><ForeName>Alicia B</ForeName><Initials>AB</Initials></Author><Author ValidYN="Y"><LastName>Lockhart</LastName><ForeName>María T</ForeName><Initials>MT</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>11</Month><Day>22</Day></ArticleDate></Article><MedlineJournalInfo><Country>Netherlands</Country><MedlineTA>Ultrason Sonochem</MedlineTA><NlmUniqueID>9433356</NlmUniqueID><ISSNLinking>1350-4177</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Hydrocarbons, Chlorinated</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Ketones</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Tin Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>045A6V3VFX</RegistryNumber><NameOfSubstance>Indium</NameOfSubstance></Chemical><Chemical><RegistryNumber>2406-52-2</RegistryNumber><NameOfSubstance>stannane</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Hydrocarbons, Chlorinated</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Ketones</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName MajorTopicYN="N">chemistry</QualifierName><QualifierName MajorTopicYN="N">radiation effects</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="Y">Sonication</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Sound</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Tin Compounds</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName><QualifierName MajorTopicYN="N">radiation effects</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2012</Year><Month>7</Month><Day>3</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2012</Year><Month>10</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2012</Year><Month>10</Month><Day>31</Day></PubMedPubDate><PubMedPubDate PubStatus="aheadofprint"><Year>2012</Year><Month>11</Month><Day>22</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>12</Month><Day>11</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>12</Month><Day>12</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2013</Year><Month>7</Month><Day>6</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pii">S1350-4177(12)00244-1</ArticleId><ArticleId IdType="doi">10.1016/j.ultsonch.2012.10.018</ArticleId><ArticleId IdType="pubmed">23219615</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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