Dual hard/soft gold catalysis: intermolecular Friedel-Crafts-type α-amidoalkylation/alkyne hydroarylation sequences by N-acyliminium ion chemistry.
Identifieur interne : 000327 ( Ncbi/Checkpoint ); précédent : 000326; suivant : 000328Dual 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
Affiliations:
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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><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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