Following Formation

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Science  11 Jul 2003:
Vol. 301, Issue 5630, pp. 143
DOI: 10.1126/science.301.5630.143b

High-throughput screening is increasingly being used to evaluate the performance of many catalysts. Such screening would be facilitated if the desired reaction could be tracked via a spectroscopic signal, such as fluorescence. For monitoring carbon-carbon bond cleavage, there are several probes whose fluorescence increases, but it is more difficult to follow the formation of carbon-carbon bonds in the same fashion.

Using a compound previously used to detect carbon-sulfur bond formation as one of the reactants, Tanaka et al. show that for Michael and Diels-Alder synthetic reactions, fluorescence increases by a factor of 20 to 100 upon carbon-carbon bond formation. The fluorescence signal allows the relative reaction rates for different catalysts to be determined quickly. This class of compound (amides of α,β-unsaturated carbonyls) can be used to optimize solvent conditions and to screen protein, peptide, and small-molecule catalysts. — JFU

J. Am. Chem. Soc. 10.1021/ja034069t (2003).

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