January 20, 2011

Site-Selective, Cleavable Linkers: Quality Control and the Characterization of Small Molecules on Microelectrode Arrays

Bi, Bo; Huang, Richard Y.-C.; Maurer, Karl; Chen, Ceng; Moeller, Kevin D.

Journal of Organic Chemistry 2011, 76(21), 9053-9059

A “safety-catch” linker strategy has been used to release a portion of the products of a Diels-Alder reaction conducted on a microelectrode array for characterization of stereochem.  The attachment and cleavage of org. compds. from the surface of selected electrodes in the array can be accomplished by site-selective generation of base or acid at the electrode.  It was found that the surface of the array had a minor influence on the stereochem. of the Diels-Alder reaction, leading to slightly more of the exo-product relative to a similar soln.-phase reaction.