Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes.
Identifieur interne : 001152 ( Main/Exploration ); précédent : 001151; suivant : 001153Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes.
Auteurs : RBID : pubmed:21338129English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Ketones.
- chemical , chemistry : Chlorobenzenes, Indicators and Reagents, Indium, Ketones, Tin Compounds.
- Catalysis, Substrate Specificity.
Abstract
Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.
DOI: 10.1021/jo102366q
PubMed: 21338129
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Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">21338129</PMID><DateCreated><Year>2011</Year><Month>03</Month><Day>11</Day></DateCreated><DateCompleted><Year>2011</Year><Month>06</Month><Day>21</Day></DateCompleted><DateRevised><Year>2013</Year><Month>11</Month><Day>21</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>76</Volume><Issue>6</Issue><PubDate><Year>2011</Year><Month>Mar</Month><Day>18</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Selective synthetic routes to sterically hindered unsymmetrical diaryl ketones via arylstannanes.</ArticleTitle><Pagination><MedlinePgn>1707-14</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo102366q</ELocationID><Abstract><AbstractText>Bulky arylstannanes and bulky aroyl chlorides are good reaction partners for the synthesis of two-, three-, and even four-ortho-substituted benzophenones, in good to excellent isolated yields (47-91%). Three simple and direct routes, with differential advantages, are proposed: (i) a catalyst-free protocol, in o-dichlorobenzene (ODCB) at 180 °C; (ii) a room temperature protocol, using AlCl(3) (0.5 equiv), in dichloromethane (DCM); and (iii) a solvent-free, indium-promoted procedure. A radical mechanism is proposed for the indium-mediated reactions.</AbstractText></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>Silbestri</LastName><ForeName>Gustavo F</ForeName><Initials>GF</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>2011</Year><Month>02</Month><Day>22</Day></ArticleDate></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>Chlorobenzenes</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance>Indicators and Reagents</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><Chemical><RegistryNumber>K18102WN1G</RegistryNumber><NameOfSubstance>chlorobenzene</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Catalysis</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Chlorobenzenes</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indicators and Reagents</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName><QualifierName MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Ketones</DescriptorName><QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Substrate Specificity</DescriptorName></MeshHeading><MeshHeading><DescriptorName MajorTopicYN="N">Tin Compounds</DescriptorName><QualifierName MajorTopicYN="Y">chemistry</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2011</Year><Month>2</Month><Day>22</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2011</Year><Month>2</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2011</Year><Month>2</Month><Day>23</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2011</Year><Month>6</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo102366q</ArticleId><ArticleId IdType="pubmed">21338129</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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