Urea-Induced Acid Amplification: A New Approach for Metal-Free Insertion Chemistry

被引：25

作者：

Couch, Erica D. ^{[1
]}

Auvil, Tyler J. ^{[1
]}

Mattson, Anita E. ^{[1
]}

机构：

[1] Ohio State Univ, Dept Chem & Biochem, Columbus, OH 43210 USA

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 27期

关键词：

acidity; diazo compounds; insertion; organocatalysis; urea; PICTET-SPENGLER REACTIONS; ASYMMETRIC INTRAMOLECULAR CYCLOPROPANATION; HIGHLY ENANTIOSELECTIVE INSERTION; ALPHA-DIAZOCARBONYL COMPOUNDS; STABILIZED BRONSTED ACIDS; S HYDROGEN-BONDS; O-H BONDS; COOPERATIVE CATALYSIS; COMPLEXES; PROLINE;

D O I：

10.1002/chem.201403283

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enhanced catalytic activity of difluoroboronate ureas proved to be essential as an acidity amplifier to promote metal-free O-H and S-H insertion reactions of alpha-aryldiazoacetates in high yield. This methodology was found to be generally applicable to a broad substrate scope and presents a conceptually new approach for organocatalytic diazo insertion reactions. Mechanistic investigations suggest that the reaction pathway involves a urea-induced protonation of the alpha-aryldiazoester.

引用

页码：8283 / 8287

页数：5

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