Enolizable Carbonyls and N,O-Acetals: A Rational Approach for Room-Temperature Lewis Superacid-Catalyzed Direct α-Amidoalkylation of Ketones and Aldehydes.
Identifieur interne : 000066 ( Main/Exploration ); précédent : 000065; suivant : 000067Enolizable 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
Affiliations:
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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 Naturelles et à l'Environnement-, LACReSNE-Faculté des Sciences de Bizerte-, 7021, Bizerte, Université de Carthage</wicri:regionArea><wicri:noRegion>Université de Carthage</wicri:noRegion></affiliation></author><author><name sortKey="Antoniotti, Sylvain" sort="Antoniotti, Sylvain" uniqKey="Antoniotti S" first="Sylvain" last="Antoniotti">Sylvain Antoniotti</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="Du Ach, Elisabet" sort="Du Ach, Elisabet" uniqKey="Du Ach E" 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><affiliations><list><country><li>France</li><li>Tunisie</li></country><region><li>Haute-Normandie</li><li>Provence-Alpes-Côte d'Azur</li><li>Région Normandie</li></region><settlement><li>Le Havre</li><li>Nice</li></settlement></list><tree><country name="France"><region name="Région Normandie"><name sortKey="Touati, Bahria" sort="Touati, Bahria" uniqKey="Touati B" first="Bahria" last="Touati">Bahria Touati</name></region><name sortKey="Antoniotti, Sylvain" sort="Antoniotti, Sylvain" uniqKey="Antoniotti S" first="Sylvain" last="Antoniotti">Sylvain Antoniotti</name><name sortKey="Dalla, Vincent" sort="Dalla, Vincent" uniqKey="Dalla V" first="Vincent" 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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