LeHavreV1, Main, Exploration, bibRecord, 000670

Dual Hard/Soft Gold Catalysis: Intermolecular Friedel–Crafts‐Type α‐Amidoalkylation/Alkyne Hydroarylation Sequences by N‐Acyliminium Ion Chemistry

Identifieur interne : 000670 ( Main/Exploration ); précédent : 000669; suivant : 000671

Dual Hard/Soft Gold Catalysis: Intermolecular Friedel–Crafts‐Type α‐Amidoalkylation/Alkyne Hydroarylation Sequences by N‐Acyliminium Ion Chemistry

Auteurs : Liliana Boiaryna ; El Mkaddem ; Taillier ; Dalla ; Othman

Source :

Chemistry – A European Journal [ 0947-6539 ] ; 2012-10-29.

RBID : ISTEX:2E239827506F0F72489B45189D94CE95DD11D3B1

English descriptors

KwdEn :
- gold, homogeneous catalysis, hydroarylation, nitrogen heterocycles, reaction mechanisms.

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.

Url:

https://api.istex.fr/document/2E239827506F0F72489B45189D94CE95DD11D3B1/fulltext/pdf

DOI: 10.1002/chem.201202225

Affiliations:

Le document en format XML

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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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Dual Hard/Soft Gold Catalysis: Intermolecular Friedel–Crafts‐Type α‐Amidoalkylation/Alkyne Hydroarylation Sequences by N‐Acyliminium Ion Chemistry

Dual Hard/Soft Gold Catalysis: Intermolecular Friedel–Crafts‐Type α‐Amidoalkylation/Alkyne Hydroarylation Sequences by N‐Acyliminium Ion Chemistry

Source :

English descriptors

Abstract

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Le document en format XML

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