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

ORGN 538

Roman V. Rozhkov, V. Jo Davisson, and Donald E. Bergstrom. Bindley Bioscience Center, Birck Nanotechnology Center and Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, IN 47906
We have developed novel fluorogenic transformations based on formation of C-C bond catalyzed by palladium using iodocoumarin 1 as a model aryl iodide, where fluorescence is quenched completely due to effects of 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.

 

Materials, Devices and Switches, Metal-Mediated Reactions, Asymmetric Reactions, Total Synthesis, Biologically-Related Molecules and Processes
7:00 PM-9:00 PM, Wednesday, April 9, 2008 Morial Convention Center -- La Louisiane, Blrm. C, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008