Rapid Electrochemical Deprotection of the Iso­nicotinyl­oxycarbonyl Group from Carbonates and Thiocarbonates in a Microfluidic Reactor

Abstract

Electro­reductive deprotection of the iso­nicotinyl­oxy­carbonyl (<i>i</i>Noc) group from hydroxy, thiol, and amino groups was carried out in an electro­chemical micro­reactor. The small distance of the platinum electrodes in the micro­reactor enables a rapid electro­chemical redox reaction without added electrolytes. As a result, the electro­chemical deprotection of <i>O</i>- and <i>S</i>-<i>i</i>Noc aromatic substrates was achieved in short reaction times (<2 min), while <i>N</i>-<i>i</i>Noc and non­aromatic substrates did not react under the same reaction conditions. This method enables a rapid and site-selective deprotection of <i>O</i>- or <i>S</i>-<i>i</i>Noc groups without removal of <i>N</i>-<i>i</i>Noc moieties