Electroorganic Synthesis Enabled by an Automated Flow Platform

Abstract

Lately, electroorganic chemistry has received the attention of chemists due to its efficiency and ability to form organic molecules by adding or removing electrons. In addition, microreactors and flow platforms are successfully engaged to offer practical solutions for the typical limitations of batch electrolysis. Our laboratory has made significant contributions to this area by developing and producing home-made electrochemical flow reactors and showing their applications in various synthetic transformations. These developments were successfully achieved but the developed reactors suffered from some limitations that affect standardization of the reaction process development. The continuous quest to develop standard electrochemical equipment, led to development of the Ion electrochemical reactor by the flow technology company, Vapourtec, in collaboration with our laboratory. This reactor was developed to be more robust and easier to use. The first part of my work was the assessment of the performance and reliability of the Ion reactor prototype before its commercialization. The Shono oxidation was used as a model reaction and the results were compared to the previously published results for the same reaction using other flow electrochemical reactors.The Ion reactor was then integrated with a fully automated flow system. This platform was utilised for selenenylation reactions of alkenes. The automation allowed multiple electrochemical reactions to be performed in a fully autonomous way. Similarly, the automated electrochemical flow system has been utilised for chalcogenophosphite formation.Also, an efficient electrochemical flow processes for the selective oxidation of sulfides to sulfoxides and sulfones, in addition to oxidation of sulfoxides to N-cyanosulfoximines have been developed.The synthesis was facilitated by the fully automated electrochemical protocol.