Importance of ortho Proton Donors in Catalysis of Hydrazone Formation

被引：89

作者：

Crisalli, Pete ^{[1
]}

Kool, Eric T. ^{[1
]}

机构：

[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 07期

基金：

美国国家卫生研究院;

关键词：

DYNAMIC COVALENT CHEMISTRY; NUCLEOPHILIC CATALYSIS; SEMICARBAZONE FORMATION; AQUEOUS-SOLUTIONS; OXIME FORMATION; LIGATION; ANILINES; SYSTEMS; WATER; ACID;

D O I：

10.1021/ol400427x

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Anthranilic acids were recently reported as superior catalysts for hydrazone and oxime formation compared to aniline, the classic catalyst for these reactions. Here, alternative proton donors were examined with varied pK(a) in an effort to enhance activity at biological pH. The experiments show that 2-aminobenzenephosphonic acids are superior to anthranilic acids in catalyzing hydrazone formation with common aldehyde substrates.

引用

收藏

页码：1646 / 1649

页数：4

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