Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.
Identifieur interne : 000038 ( PubMed/Checkpoint ); précédent : 000037; suivant : 000039Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.
Auteurs : Bahria Touati [France] ; Abderrahman El Bouakher [France] ; Catherine Taillier [France] ; Raja Ben Othman [Tunisie] ; Malika Trabelsi-Ayadi [Tunisie] ; Sylvain Antoniotti [France] ; Elisabet Du Ach [France] ; Vincent Dalla [France]Source :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2016.
Abstract
An efficient catalytic room-temperature direct α-amidoalkylation of carbonyl donors, that is, ketones and aldehydes with unbiased N,O-acetals, is described. Sn(NTf2 )4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope. A comprehensive and rational evaluation of this reaction has led to the establishment of an empirical scale of nucleophilic reactivity for a broad set of ketones that should be helpful in the synthetic design and development of carbonyl α-functionalization methods.
DOI: 10.1002/chem.201504772
PubMed: 26992138
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CNRS, URCOM, 76600, Le Havre, France. vincent.dalla@univ-lehavre.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2016">2016</date><idno type="RBID">pubmed:26992138</idno><idno type="pmid">26992138</idno><idno type="doi">10.1002/chem.201504772</idno><idno type="wicri:Area/PubMed/Corpus">000042</idno><idno type="wicri:Area/PubMed/Curation">000042</idno><idno type="wicri:Area/PubMed/Checkpoint">000042</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.</title><author><name sortKey="Touati, Bahria" sort="Touati, Bahria" uniqKey="Touati B" first="Bahria" last="Touati">Bahria Touati</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="El Bouakher, Abderrahman" sort="El Bouakher, Abderrahman" uniqKey="El Bouakher A" first="Abderrahman" last="El Bouakher">Abderrahman El Bouakher</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="Taillier, Catherine" sort="Taillier, Catherine" uniqKey="Taillier C" first="Catherine" last="Taillier">Catherine Taillier</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author><author><name sortKey="Othman, Raja Ben" sort="Othman, Raja Ben" uniqKey="Othman R" first="Raja Ben" last="Othman">Raja Ben Othman</name><affiliation wicri:level="1"><nlm:affiliation>Ecole supérieure des sciences et de technologie de Hammam Sousse, Rue Lamine Abassi, 4011H, Sousse, Tunisie.</nlm:affiliation><country xml:lang="fr">Tunisie</country><wicri:regionArea>Ecole supérieure des sciences et de technologie de Hammam Sousse, Rue Lamine Abassi, 4011H, Sousse</wicri:regionArea><wicri:noRegion>Sousse</wicri:noRegion></affiliation></author><author><name sortKey="Trabelsi Ayadi, Malika" sort="Trabelsi Ayadi, Malika" uniqKey="Trabelsi Ayadi M" first="Malika" last="Trabelsi-Ayadi">Malika Trabelsi-Ayadi</name><affiliation wicri:level="1"><nlm:affiliation>Laboratoire d'Application de la Chimie aux Ressources et Substances Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage, Tunisie.</nlm:affiliation><country xml:lang="fr">Tunisie</country><wicri:regionArea>Laboratoire d'Application de la Chimie aux Ressources et Substances 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first="Elisabet" last="Du Ach">Elisabet Du Ach</name><affiliation wicri:level="3"><nlm:affiliation>Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2, France.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2</wicri:regionArea><placeName><region type="region" nuts="2">Provence-Alpes-Côte d'Azur</region><settlement type="city">Nice</settlement></placeName></affiliation></author><author><name sortKey="Dalla, Vincent" sort="Dalla, Vincent" uniqKey="Dalla V" first="Vincent" last="Dalla">Vincent Dalla</name><affiliation wicri:level="3"><nlm:affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France. vincent.dalla@univ-lehavre.fr.</nlm:affiliation><country xml:lang="fr">France</country><wicri:regionArea>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre</wicri:regionArea><placeName><region type="region" nuts="2">Région Normandie</region><region type="old region" nuts="2">Haute-Normandie</region><settlement type="city">Le Havre</settlement></placeName></affiliation></author></analytic><series><title level="j">Chemistry (Weinheim an der Bergstrasse, Germany)</title><idno type="eISSN">1521-3765</idno><imprint><date when="2016" type="published">2016</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">An efficient catalytic room-temperature direct α-amidoalkylation of carbonyl donors, that is, ketones and aldehydes with unbiased N,O-acetals, is described. Sn(NTf2 )4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope. A comprehensive and rational evaluation of this reaction has led to the establishment of an empirical scale of nucleophilic reactivity for a broad set of ketones that should be helpful in the synthetic design and development of carbonyl α-functionalization methods.</div></front></TEI><pubmed><MedlineCitation Status="PubMed-not-MEDLINE" Owner="NLM"><PMID Version="1">26992138</PMID><DateCreated><Year>2016</Year><Month>4</Month><Day>13</Day></DateCreated><DateCompleted><Year>2016</Year><Month>08</Month><Day>16</Day></DateCompleted><DateRevised><Year>2016</Year><Month>4</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3765</ISSN><JournalIssue CitedMedium="Internet"><Volume>22</Volume><Issue>17</Issue><PubDate><Year>2016</Year><Month>Apr</Month><Day>18</Day></PubDate></JournalIssue><Title>Chemistry (Weinheim an der Bergstrasse, Germany)</Title><ISOAbbreviation>Chemistry</ISOAbbreviation></Journal><ArticleTitle>Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.</ArticleTitle><Pagination><MedlinePgn>6012-22</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1002/chem.201504772</ELocationID><Abstract><AbstractText>An efficient catalytic room-temperature direct α-amidoalkylation of carbonyl donors, that is, ketones and aldehydes with unbiased N,O-acetals, is described. Sn(NTf2 )4 is an optimal catalyst to promote this challenging transformation at low loading and the reaction shows promising scope. A comprehensive and rational evaluation of this reaction has led to the establishment of an empirical scale of nucleophilic reactivity for a broad set of ketones that should be helpful in the synthetic design and development of carbonyl α-functionalization methods.</AbstractText><CopyrightInformation>© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Touati</LastName><ForeName>Bahria</ForeName><Initials>B</Initials><AffiliationInfo><Affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>Laboratoire d'Application de la Chimie aux Ressources et Substances Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage, Tunisie.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>El Bouakher</LastName><ForeName>Abderrahman</ForeName><Initials>A</Initials><AffiliationInfo><Affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Taillier</LastName><ForeName>Catherine</ForeName><Initials>C</Initials><AffiliationInfo><Affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Othman</LastName><ForeName>Raja Ben</ForeName><Initials>RB</Initials><AffiliationInfo><Affiliation>Ecole supérieure des sciences et de technologie de Hammam Sousse, Rue Lamine Abassi, 4011H, Sousse, Tunisie.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Trabelsi-Ayadi</LastName><ForeName>Malika</ForeName><Initials>M</Initials><AffiliationInfo><Affiliation>Laboratoire d'Application de la Chimie aux Ressources et Substances Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage, Tunisie.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Antoniotti</LastName><ForeName>Sylvain</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Duñach</LastName><ForeName>Elisabet</ForeName><Initials>E</Initials><AffiliationInfo><Affiliation>Institut de Chimie de Nice, UMR 7272, Université de Nice Sophia Antipolis, C.N.R.S., Parc Valrose, 06108, Nice cedex 2, France.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Dalla</LastName><ForeName>Vincent</ForeName><Initials>V</Initials><Identifier Source="ORCID">http://orcid.org/0000-0001-9043-5996</Identifier><AffiliationInfo><Affiliation>Normandie Univ., UNIHAVRE, CNRS, URCOM, 76600, Le Havre, France. vincent.dalla@univ-lehavre.fr.</Affiliation></AffiliationInfo></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2016</Year><Month>Mar</Month><Day>15</Day></ArticleDate></Article><MedlineJournalInfo><Country>Germany</Country><MedlineTA>Chemistry</MedlineTA><NlmUniqueID>9513783</NlmUniqueID><ISSNLinking>0947-6539</ISSNLinking></MedlineJournalInfo><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Lewis acids</Keyword><Keyword MajorTopicYN="N">alkylation</Keyword><Keyword MajorTopicYN="N">enols</Keyword><Keyword MajorTopicYN="N">lactams</Keyword><Keyword MajorTopicYN="N">superacidic systems</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2015</Year><Month>11</Month><Day>26</Day></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2016</Year><Month>3</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2016</Year><Month>3</Month><Day>19</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate 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last="Dalla">Vincent Dalla</name><name sortKey="Du Ach, Elisabet" sort="Du Ach, Elisabet" uniqKey="Du Ach E" first="Elisabet" last="Du Ach">Elisabet Du Ach</name><name sortKey="El Bouakher, Abderrahman" sort="El Bouakher, Abderrahman" uniqKey="El Bouakher A" first="Abderrahman" last="El Bouakher">Abderrahman El Bouakher</name><name sortKey="Taillier, Catherine" sort="Taillier, Catherine" uniqKey="Taillier C" first="Catherine" last="Taillier">Catherine Taillier</name></country><country name="Tunisie"><noRegion><name sortKey="Othman, Raja Ben" sort="Othman, Raja Ben" uniqKey="Othman R" first="Raja Ben" last="Othman">Raja Ben Othman</name></noRegion><name sortKey="Trabelsi Ayadi, Malika" sort="Trabelsi Ayadi, Malika" uniqKey="Trabelsi Ayadi M" first="Malika" last="Trabelsi-Ayadi">Malika Trabelsi-Ayadi</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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