Fluorogenic transformations based on formation of C-C bonds catalyzed by palladium: An efficient approach for high throughput optimizations and kinetic studies

Roman V. Rozhkov, Purdue University
Vincent J. Davisson, Purdue University
Donald E. Bergstrom, Birck Nanotechnology Center and Bindley Bioscience Center, Purdue University

Abstract

We have developed novel fluorogenic transformations based on formation of C-C bonds catalyzed by palladium using iodocoumarin I as a model aryl iodide, where fluorescence is quenched completely due to effects of the heavy, polarizable iodine atom. Substitution of the iodine atom for the carbon using Sonogashira, Suzuki-Miyaura and Heck couplings results in a dramatic fluorescence enhancement. This approach has been used successfully for the optimization of reaction conditions and kinetic studies in high throughput format.