Fluorescent detection of carbon-carbon bond formation.
Fluorescent detection of carbon-carbon bond formation.
复制标题
碳-碳键形成的荧光检测。
DOI：
10.1021/ja034069t
复制
发表时间：
2003
期刊：
影响因子：
--
通讯作者：
Barbas3rd,CarlosF
中科院分区：
文献类型：
--
作者：
Tanaka,Fujie;Thayumanavan,Rajeswari;Barbas3rd,CarlosF
我们开发了一种新的光谱系统，用于通过荧光检测碳-碳键的形成，以提高高通量催化剂筛选和小规模催化剂的快速表征。由具有氨基的荧光团组成的荧光底物容易制备为α，β-不饱和羰基化合物的酰胺，并且通常表现出低荧光，而这些荧光底物的Michael或Diels-桤木反应提供荧光显著增加的产物。产物的荧光比底物高约20至100倍。通过筛选迈克尔反应的潜在催化剂和溶剂优化实验验证了该测定系统。具有氨基的荧光团与α，β-不饱和羰基化合物的共价组合应提供多种荧光底物，其可用于快速筛选催化剂和优化反应条件。
We have developed a new spectroscopic system for detecting carbon−carbon bond formation by fluorescence to enhance high-throughput catalyst screening and rapid characterization of catalysts on a small scale. Fluorogenic substrates composed of a fluorophore possessing an amino group are readily prepared as amides of α,β-unsaturated carbonyl compounds and generally exhibit low fluorescence, while Michael or Diels−Alder reactions of these fluorogenic substrates provide products of significantly increased fluorescence. The product's fluorescence is approximately 20- to 100-fold higher than that of the substrate. The assay system was validated by screening potential catalysts of the Michael reaction and in solvent optimization experiments. The covalent combination of fluorophores possessing an amino group with α,β-unsaturated carbonyl compounds should provide a diverse range of fluorogenic substrates that may be used to rapidly screen catalysts and to optimize reaction conditions.