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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<front><div type="abstract" xml:lang="en">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.</div>
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