Cu(I)-catalysed N-H insertion in water: a new tool for chemical biology

被引：28

作者：

Tishinov, Kiril ^{[1
]}

Fei, Na ^{[1
]}

Gillingham, Dennis ^{[1
]}

机构：

[1] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

CHEMICAL SCIENCE | 2013年 / 4卷 / 12期

关键词：

CLICK CHEMISTRY; DIAZO-COMPOUNDS; TERMINAL ALKYNES; DNA; CATALYSIS; RNA; CYCLOADDITION; COORDINATION; CARBENOIDS; SYSTEM;

D O I：

10.1039/c3sc51363g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

We demonstrate for the first time that Cu(I)-catalysis can deliver N-H insertion (NHI) with alpha-diazocarbonyl compounds in aqueous media. Despite being carried out in water only trace amounts of O-H insertion are seen, indicating the catalyst's overwhelming preference for NHI. Our optimized conditions for NHI converged with those used for the Cu-catalyzed azide-alkyne cycloaddition (CuAAC) for bioconjugation, spurring us to develop an auto-tandem catalytic process where both catalytic cycles operate simultaneously in one-pot. We explore the scope of the method with both small molecule and complex DNA and RNA substrates.

引用

页码：4401 / 4406

页数：6

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