Dual hard/soft gold catalysis: intermolecular Friedel-Crafts-type α-amidoalkylation/alkyne hydroarylation sequences by N-acyliminium ion chemistry.
Identifieur interne : 000190 ( PubMed/Checkpoint ); précédent : 000189; suivant : 000191Dual hard/soft gold catalysis: intermolecular Friedel-Crafts-type α-amidoalkylation/alkyne hydroarylation sequences by N-acyliminium ion chemistry.
Auteurs : Liliana Boiaryna [France] ; Mohamed Kamal El Mkaddem ; Catherine Taillier ; Vincent Dalla ; Mohamed OthmanSource :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2012.
Abstract
Gold catalysts have been applied in cascade-type reactions for the synthesis of different nitrogen-based compounds. The reactions likely proceed by a new gold-catalyzed cascade intermolecular α-amidoalkylation/intramolecular carbocyclization cascade process by unifying both the σ- and π-Lewis acid properties of the gold salts. In the first part of this report we show that the σ-Lewis acidity of gold(I) and gold(III) could be exploited to efficiently catalyze the nucleophilic substitution of various alkoxy- and acetoxylactams. The reaction was found to be applicable to a wide range of cyclic N-acyliminium ion precursors and various nucleophiles, including allyltrimethylsilane, silyl enol ethers, arenes, and active methylene derivatives. As a logical progression of this study, a combined hard/soft binary catalytic gold system was then used to implement an unprecedented tandem intermolecular Friedel-Crafts amidoalkylation/intramolecular hydroarylation sequence allowing an expedient access to new, complex, fused polyheterocyclic structures from trivial materials.
DOI: 10.1002/chem.201202225
PubMed: 22996700
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The reactions likely proceed by a new gold-catalyzed cascade intermolecular α-amidoalkylation/intramolecular carbocyclization cascade process by unifying both the σ- and π-Lewis acid properties of the gold salts. In the first part of this report we show that the σ-Lewis acidity of gold(I) and gold(III) could be exploited to efficiently catalyze the nucleophilic substitution of various alkoxy- and acetoxylactams. The reaction was found to be applicable to a wide range of cyclic N-acyliminium ion precursors and various nucleophiles, including allyltrimethylsilane, silyl enol ethers, arenes, and active methylene derivatives. As a logical progression of this study, a combined hard/soft binary catalytic gold system was then used to implement an unprecedented tandem intermolecular Friedel-Crafts amidoalkylation/intramolecular hydroarylation sequence allowing an expedient access to new, complex, fused polyheterocyclic structures from trivial materials.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">22996700</PMID><DateCreated><Year>2012</Year><Month>10</Month><Day>22</Day></DateCreated><DateCompleted><Year>2013</Year><Month>03</Month><Day>14</Day></DateCompleted><DateRevised><Year>2012</Year><Month>10</Month><Day>22</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>18</Volume><Issue>44</Issue><PubDate><Year>2012</Year><Month>Oct</Month><Day>29</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Dual hard/soft gold catalysis: intermolecular Friedel-Crafts-type α-amidoalkylation/alkyne hydroarylation sequences by N-acyliminium ion chemistry.</ArticleTitle><Pagination><MedlinePgn>14192-200</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201202225</ELocationID><Abstract><AbstractText>Gold catalysts have been applied in cascade-type reactions for the synthesis of different nitrogen-based compounds. The reactions likely proceed by a new gold-catalyzed cascade intermolecular α-amidoalkylation/intramolecular carbocyclization cascade process by unifying both the σ- and π-Lewis acid properties of the gold salts. In the first part of this report we show that the σ-Lewis acidity of gold(I) and gold(III) could be exploited to efficiently catalyze the nucleophilic substitution of various alkoxy- and acetoxylactams. The reaction was found to be applicable to a wide range of cyclic N-acyliminium ion precursors and various nucleophiles, including allyltrimethylsilane, silyl enol ethers, arenes, and active methylene derivatives. As a logical progression of this study, a combined hard/soft binary catalytic gold system was then used to implement an unprecedented tandem intermolecular Friedel-Crafts amidoalkylation/intramolecular hydroarylation sequence allowing an expedient access to new, complex, fused polyheterocyclic structures from trivial materials.</AbstractText><CopyrightInformation>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Boiaryna</LastName><ForeName>Liliana</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>URCOM, EA,CNRS, FR, Université du Havre, Le Havre, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>El Mkaddem</LastName><ForeName>Mohamed Kamal</ForeName><Initials>MK</Initials></Author><Author ValidYN="Y"><LastName>Taillier</LastName><ForeName>Catherine</ForeName><Initials>C</Initials></Author><Author ValidYN="Y"><LastName>Dalla</LastName><ForeName>Vincent</ForeName><Initials>V</Initials></Author><Author ValidYN="Y"><LastName>Othman</LastName><ForeName>Mohamed</ForeName><Initials>M</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2012</Year><Month>Sep</Month><Day>20</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2012</Year><Month>6</Month><Day>22</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2012</Year><Month>7</Month><Day>27</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2012</Year><Month>9</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2012</Year><Month>9</Month><Day>22</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2012</Year><Month>9</Month><Day>22</Day><Hour>6</Hour><Minute>1</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">22996700</ArticleId><ArticleId IdType="doi">10.1002/chem.201202225</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Dalla, Vincent" sort="Dalla, Vincent" uniqKey="Dalla V" first="Vincent" last="Dalla">Vincent Dalla</name><name sortKey="El Mkaddem, Mohamed Kamal" sort="El Mkaddem, Mohamed Kamal" uniqKey="El Mkaddem M" first="Mohamed Kamal" last="El Mkaddem">Mohamed Kamal El Mkaddem</name><name sortKey="Othman, Mohamed" sort="Othman, Mohamed" uniqKey="Othman M" first="Mohamed" last="Othman">Mohamed Othman</name><name sortKey="Taillier, Catherine" sort="Taillier, Catherine" uniqKey="Taillier C" first="Catherine" last="Taillier">Catherine Taillier</name></noCountry><country name="France"><noRegion><name sortKey="Boiaryna, Liliana" sort="Boiaryna, Liliana" uniqKey="Boiaryna L" first="Liliana" last="Boiaryna">Liliana Boiaryna</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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