Process for performing an isolated Pd(0) catalyzed reaction electrochemically on an electrode array device
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example 1
[0039] This example tested the feasibility of the inventive process. The experiment outlined in FIG. 2 was performed. First, an aryl iodide was placed on the surface of an electrode array device (Combimatrix Corporation, Mukilteo, Wash.) coated with polysaccharide, and then the electrode array device was submerged in an electrolyte solution containing 1-pyrenemethyl acrylate, palladium acetate, triphenylphoshine ligand, and allyl methyl carbonate. Selected cathodes were used to reduce the palladium acetate to the desired Pd(0) catalyst. If there was successful reduction, the Pd(0) catalyst generate would trigger a Heck reaction between the surface-bound aryl iodide the 1-pyrenemethyl acrylate, but only at those electrode sites whose electrodes were activated as a cathode. A successful Heck reaction would place the fluorescent pyrene moiety onto the surface of the electrode array device, but only in the region surrounding an electrode. This creates the ability to monitor the success ...
example 2
[0041] A series of solution phase Heck reactions were performed in order to determine reaction conditions that would allow for an electrochemically generated Heck reaction. Two key discoveries were made along these lines. First, a Heck reaction between methyl 4-iodobenzoate and 1-pyrenemethyl acrylate proceeded slowly (18 h / 82% yield) with Pd(OAc)2 in a 9:1 DMF:H2O solution containing triethylamine and tetrabutylammonium bromide while the same reaction proceeded to completion in just 3 h when a cathode was inserted and the Pd(OAc)2 reduced electrochemically. Second, the Heck reaction did not proceed at all (0% after 18 h) in the absence of the cathode when the DMF solvent was exchanged for acetonitrile. The corresponding electrochemical reaction proceeded to completion (76% yield) in 12 hours. Hence, using acetonitrile as the solvent for the reactions would assure that the Heck reaction would not spontaneously occur at sites on the electrode array device without a working cathode. E...
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