Chemoselective deprotonative lithiation of azobenzenes: reactions and mechanisms.
Identifieur interne : 000040 ( PubMed/Curation ); précédent : 000039; suivant : 000041Chemoselective deprotonative lithiation of azobenzenes: reactions and mechanisms.
Auteurs : Thi Thanh Thuy Nguyen [France] ; Anne Boussonnière ; Estelle Banaszak ; Anne-Sophie Castanet ; Kim Phi Phung Nguyen ; Jacques MortierSource :
- The Journal of organic chemistry [ 1520-6904 ] ; 2014.
Abstract
Whereas standard strong bases (n-BuLi, s-BuLi/TMEDA, n-BuLi/t-BuOK, TMPMgCl·LiCl, and LDA) reduce the N═N bond of the parent azobenzene (Y = H), aromatic H→Li permutation occurs with LTMP when a suitable director of lithiation (Y = OMe, CONEt2, F) is present in the benzene residue of the azo compound. The method allows direct access to new substituted azobenzenes.
DOI: 10.1021/jo500230q
PubMed: 24568538
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The method allows direct access to new substituted azobenzenes.</div></front></TEI><pubmed><MedlineCitation Owner="NLM" Status="PubMed-not-MEDLINE"><PMID Version="1">24568538</PMID><DateCreated><Year>2014</Year><Month>03</Month><Day>21</Day></DateCreated><DateCompleted><Year>2014</Year><Month>10</Month><Day>20</Day></DateCompleted><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>79</Volume><Issue>6</Issue><PubDate><Year>2014</Year><Month>Mar</Month><Day>21</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>Chemoselective deprotonative lithiation of azobenzenes: reactions and mechanisms.</ArticleTitle><Pagination><MedlinePgn>2775-80</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo500230q</ELocationID><Abstract><AbstractText>Whereas standard strong bases (n-BuLi, s-BuLi/TMEDA, n-BuLi/t-BuOK, TMPMgCl·LiCl, and LDA) reduce the N═N bond of the parent azobenzene (Y = H), aromatic H→Li permutation occurs with LTMP when a suitable director of lithiation (Y = OMe, CONEt2, F) is present in the benzene residue of the azo compound. The method allows direct access to new substituted azobenzenes.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Nguyen</LastName><ForeName>Thi Thanh Thuy</ForeName><Initials>TT</Initials><AffiliationInfo><Affiliation>Institut des Molécules et Matériaux du Mans, Faculté des Sciences et Techniques, Université du Maine and CNRS UMR 6283 , Avenue Olivier Messiaen, 72085 Le Mans Cedex 9, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Boussonnière</LastName><ForeName>Anne</ForeName><Initials>A</Initials></Author><Author ValidYN="Y"><LastName>Banaszak</LastName><ForeName>Estelle</ForeName><Initials>E</Initials></Author><Author ValidYN="Y"><LastName>Castanet</LastName><ForeName>Anne-Sophie</ForeName><Initials>AS</Initials></Author><Author ValidYN="Y"><LastName>Nguyen</LastName><ForeName>Kim Phi Phung</ForeName><Initials>KP</Initials></Author><Author ValidYN="Y"><LastName>Mortier</LastName><ForeName>Jacques</ForeName><Initials>J</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2014</Year><Month>03</Month><Day>10</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="aheadofprint"><Year>2014</Year><Month>3</Month><Day>10</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2014</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2014</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2014</Year><Month>2</Month><Day>27</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="doi">10.1021/jo500230q</ArticleId><ArticleId IdType="pubmed">24568538</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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