Modular Pyridine Synthesis from Oximes and Enals through Synergistic Copper/Iminium Catalysis

被引：266

作者：

Wei, Ye ^{[1
]}

Yoshikai, Naohiko ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 10期

基金：

新加坡国家研究基金会;

关键词：

ONE-POT SYNTHESIS; TRANSITION-METAL; ALPHA; BETA-UNSATURATED KETOXIMES; ALDEHYDES; ALKYNES; COMBINATION; ALKYLATION; SALTS; 2,4,6-TRIARYLPYRIDINES; CYCLOADDITION;

D O I：

10.1021/ja312346s

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We describe here a [3+3]-type condensation reaction of O-acetyl ketoximes and alpha,beta-unsaturated aldehydes that is synergistically catalyzed by a copper(I) salt and a secondary ammonium salt (or amine). This redox-neutral reaction allows modular synthesis of a variety of substituted pyridines under mild conditions with tolerance of a broad range of functional groups. The reaction is driven by a merger of iminium catalysis and redox activity of the copper catalyst, which would initially reduce the oxime N-O bond to generate a nucleophilic copper(II) enamide and later oxidize a dihydropyridine intermediate to the pyridine product.

引用

页码：3756 / 3759

页数：4

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