Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.
Identifieur interne : 000224 ( PubMed/Corpus ); précédent : 000223; suivant : 000225Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.
Auteurs : J. Kristensen ; M. Lysén ; P. Veds ; M. BegtrupSource :
- Organic letters [ 1523-7060 ] ; 2001.
Abstract
[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.
PubMed: 11388835
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Begtrup</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2001">2001</date><idno type="RBID">pubmed:11388835</idno><idno type="pmid">11388835</idno><idno type="wicri:Area/PubMed/Corpus">000224</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000224</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.</title><author><name sortKey="Kristensen, J" sort="Kristensen, J" uniqKey="Kristensen J" first="J" last="Kristensen">J. Kristensen</name><affiliation><nlm:affiliation>Royal Danish School of Pharmacy, Department of Medicinal Chemistry, Universitetsparken 2, DK-2100 Copenhagen, Denmark.</nlm:affiliation></affiliation></author><author><name sortKey="Lysen, M" sort="Lysen, M" uniqKey="Lysen M" first="M" last="Lysén">M. Lysén</name></author><author><name sortKey="Veds, P" sort="Veds, P" uniqKey="Veds P" first="P" last="Veds">P. Veds</name></author><author><name sortKey="Begtrup, M" sort="Begtrup, M" uniqKey="Begtrup M" first="M" last="Begtrup">M. Begtrup</name></author></analytic><series><title level="j">Organic letters</title><idno type="ISSN">1523-7060</idno><imprint><date when="2001" type="published">2001</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="PubMed-not-MEDLINE"><PMID Version="1">11388835</PMID><DateCreated><Year>2001</Year><Month>06</Month><Day>04</Day></DateCreated><DateCompleted><Year>2001</Year><Month>12</Month><Day>04</Day></DateCompleted><DateRevised><Year>2003</Year><Month>10</Month><Day>31</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">1523-7060</ISSN><JournalIssue CitedMedium="Print"><Volume>3</Volume><Issue>10</Issue><PubDate><Year>2001</Year><Month>May</Month><Day>17</Day></PubDate></JournalIssue><Title>Organic letters</Title><ISOAbbreviation>Org. Lett.</ISOAbbreviation></Journal><ArticleTitle>Synthesis of ortho substituted arylboronic esters by in situ trapping of unstable lithio intermediates.</ArticleTitle><Pagination><MedlinePgn>1435-7</MedlinePgn></Pagination><Abstract><AbstractText>[reaction: see text] Ortho lithiation-in situ boration using lithium 2,2,6,6-tetramethylpiperidide (LTMP) in combination with triisopropylborate (B(OiPr)(3)) is a highly efficient and experimentally straightforward process for the preparation of ortho substituted arylboronic esters. The mild reaction conditions allow the presence of functionalities such as ester or cyano groups or halogen substituents that are usually not compatible with the conditions used in directed ortho metalation of arenes. The arylboronic esters underwent Suzuki-type cross-coupling with a range of aryl halides, furnishing biaryls in 53-94% yield.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Kristensen</LastName><ForeName>J</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Royal Danish School of Pharmacy, Department of Medicinal Chemistry, Universitetsparken 2, DK-2100 Copenhagen, Denmark.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Lysén</LastName><ForeName>M</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Vedsø</LastName><ForeName>P</ForeName><Initials>P</Initials></Author><Author ValidYN="Y"><LastName>Begtrup</LastName><ForeName>M</ForeName><Initials>M</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>Org Lett</MedlineTA><NlmUniqueID>100890393</NlmUniqueID><ISSNLinking>1523-7052</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2001</Year><Month>6</Month><Day>5</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2001</Year><Month>6</Month><Day>5</Day><Hour>10</Hour><Minute>1</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2001</Year><Month>6</Month><Day>5</Day><Hour>10</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">11388835</ArticleId><ArticleId IdType="pii">ol015598+</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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