Snapdragon Chemistry publishes on electrochemical decarboxylative C–C couplings in batch and continuous flow in Organic Letters

In late 2016 we announced that we had been awarded a Phase I Small Business Innovation Research (SBIR) grant from the National Science Foundation (NSF) for the development of an electrochemical method for the manufacture of chemicals of interest to pharmaceutical, agricultural and fine chemical producers (Award #1645765).  This grant enabled a significant amount of research and progress towards the goal of creating flow chemistry processes and devices that could harness the power of electrochemical transformations in a manner that is easily scaled.

Progress on some aspects of this work was reported in our manuscript titled "Ni-Catalyzed Electrochemical Decarboxylative C–C Couplings in Batch and Continuous Flow" which was published in the February 12th issue of Organic Letters (link).  We submitted this work in collaboration with Professor Timothy Jamison and his group.


In this manuscript we present an electrochemically driven, nickel-catalyzed reductive coupling of N-hydroxyphthalimide esters with aryl halides. We found that the reaction proceeds under mild conditions in a divided electrochemical cell employing a tertiary amine as the reductant. This decarboxylative C(sp3)–C(sp2) bond-forming transformation exhibits excellent substrate generality and functional group compatibility. An operationally simple continuous-flow version of this transformation using a commercial electrochemical flow reactor represents a robust and scalable synthesis of value added coupling process.