ORGN 437

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 a,b-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 and conditions. Covalent combination of fluorophores possessing an amino group with a,b-unsaturated carbonyl compounds should provide a diverse range of fluorogenic substrates for the spectroscopic detection of designer reactions and catalysts.