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Fluorogenic Transformations Based on Formation of CC Bonds Catalyzed by Palladium: An Efficient Approach for High Throughput Optimizations and Kinetic Studies
Author(s) -
Rozhkov Roman V.,
Davisson V. Jo,
Bergstrom Donald E.
Publication year - 2008
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200700384
Subject(s) - chemistry , palladium , sonogashira coupling , aryl , catalysis , iodide , combinatorial chemistry , fluorescence , atom (system on chip) , heck reaction , kinetic energy , photochemistry , organic chemistry , alkyl , physics , quantum mechanics , computer science , embedded system
We have developed novel fluorogenic transformations based on formation of CC bonds catalyzed by palladium using iodocoumarin 1 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.