Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.
Identifieur interne : 002522 ( Main/Exploration ); précédent : 002521; suivant : 002523Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.
Auteurs : RBID : pubmed:17253812English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Allyl Compounds, Imines.
- chemical , chemistry : Amines, Hydrocarbons, Brominated, Indium, Ionic Liquids, Organometallic Compounds.
- Catalysis, Magnetic Resonance Spectroscopy, Molecular Structure.
Abstract
Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.
DOI: 10.1021/jo062198x
PubMed: 17253812
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<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.</title><author><name sortKey="Law, Man Chun" uniqKey="Law M">Man Chun Law</name><affiliation><nlm:affiliation>Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6.</nlm:affiliation><wicri:noCountry code="subField">Canada H3A 2K6</wicri:noCountry></affiliation></author><author><name sortKey="Cheung, Tin Wai" uniqKey="Cheung T">Tin Wai Cheung</name></author><author><name sortKey="Wong, Kwok Yin" uniqKey="Wong K">Kwok-Yin Wong</name></author><author><name sortKey="Chan, Tak Hang" uniqKey="Chan T">Tak Hang Chan</name></author></titleStmt><publicationStmt><date when="2007">2007</date><idno type="doi">10.1021/jo062198x</idno><idno type="RBID">pubmed:17253812</idno><idno type="pmid">17253812</idno><idno type="wicri:Area/Main/Corpus">002904</idno><idno type="wicri:Area/Main/Curation">002904</idno><idno type="wicri:Area/Main/Exploration">002522</idno></publicationStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Allyl Compounds (chemical synthesis)</term><term>Amines (chemistry)</term><term>Catalysis</term><term>Hydrocarbons, Brominated (chemistry)</term><term>Imines (chemical synthesis)</term><term>Indium (chemistry)</term><term>Ionic Liquids (chemistry)</term><term>Magnetic Resonance Spectroscopy</term><term>Molecular Structure</term><term>Organometallic Compounds (chemistry)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Allyl Compounds</term><term>Imines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Amines</term><term>Hydrocarbons, Brominated</term><term>Indium</term><term>Ionic Liquids</term><term>Organometallic Compounds</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Catalysis</term><term>Magnetic Resonance Spectroscopy</term><term>Molecular Structure</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">17253812</PMID><DateCreated><Year>2007</Year><Month>01</Month><Day>26</Day></DateCreated><DateCompleted><Year>2007</Year><Month>04</Month><Day>13</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-3263</ISSN><JournalIssue CitedMedium="Print"><Volume>72</Volume><Issue>3</Issue><PubDate><Year>2007</Year><Month>Feb</Month><Day>2</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Synthetic and mechanistic studies of indium-mediated allylation of imines in ionic liquids.</ArticleTitle><Pagination><MedlinePgn>923-9</MedlinePgn></Pagination><Abstract><AbstractText>Aldimines derived from aryl and non-enolizable aliphatic aldehydes were allylated with allyl bromide mediated by indium powder in [bpy][BF4] (bpy = N-butylpyridine) to give good yields of the corresponding homoallylic amines. Selective formation of monoallylated amines can be achieved by varying the amount of bromide ion additive in the form of [bpy][Br]. The transient organoindium intermediates, allylindium(I) and allylindium(III) dibromide formed in the reaction, were studied by NMR spectroscopy to explain the selectivity.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Law</LastName><ForeName>Man Chun</ForeName><Initials>MC</Initials><Affiliation>Department of Chemistry, McGill University, Montreal, Quebec, Canada H3A 2K6.</Affiliation></Author><Author ValidYN="Y"><LastName>Cheung</LastName><ForeName>Tin Wai</ForeName><Initials>TW</Initials></Author><Author ValidYN="Y"><LastName>Wong</LastName><ForeName>Kwok-Yin</ForeName><Initials>KY</Initials></Author><Author ValidYN="Y"><LastName>Chan</LastName><ForeName>Tak Hang</ForeName><Initials>TH</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType>Journal Article</PublicationType><PublicationType>Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Allyl Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Amines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Hydrocarbons, Brominated</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Imines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Ionic Liquids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Organometallic Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>045A6V3VFX</RegistryNumber><NameOfSubstance>Indium</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Allyl Compounds</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Amines</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Hydrocarbons, Brominated</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Imines</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Ionic Liquids</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Organometallic Compounds</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2007</Year><Month>1</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2007</Year><Month>4</Month><Day>17</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2007</Year><Month>1</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo062198x</ArticleId><ArticleId IdType="pubmed">17253812</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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