N-Acyliminium Ion Chemistry: Highly Efficient and Versatile Carbon-Carbon Bond Formation by Nucleophilic Substitution of Hydroxy Groups Catalyzed by Sn(NTf2)4

被引：68

作者：

Ben Othman, Raja ^{[1
]}

Affani, Radouane ^{[1
]}

Tranchant, Marie-Jose ^{[1
]}

Antoniotti, Sylvain ^{[2
]}

Dalla, Vincent ^{[1
]}

Dunach, Elisabet ^{[2
]}

机构：

[1] Univ Havre, URCOM, EA 3221, FR 3038,Fac Sci & Tech, F-76058 Le Havre, France

[2] Univ Nice Sophia Antipolis, LCMBA, UMR 6001, Inst Chim Nice,CNRS, F-06108 Nice, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2010年 / 49卷 / 04期

关键词：

acetals; catalysis; Lewis acids; N-acyliminium ions; LEWIS-ACID CATALYSTS; PROPARGYLIC ALCOHOLS; ALPHA-AMIDOALKYLATION; AROMATIC-COMPOUNDS; ACTIVE CATALYSTS; BENZYLATION; ALKYLATION; TRIFLATE; CYCLIZATIONS; DERIVATIVES;

D O I：

10.1002/anie.200906036

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presentation) Atom-economical: Unmodified hemiN,O-acetals are used in a catalytic, highly efficient α- amidoalkylation of a broad range of carbon-centered nucleophiles, including silicon-based components, active methylene derivatives, electron-rich arenes, and even simple ketones (see scheme). The reactions proceed in a highly efficient manner and typically require only 1 mol% of the Lewis super-acidic reagent Sn(NTf2)4 as the catalyst. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：776 / 780

页数：5

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