Electrosynthesis: A Practical Way to Access Highly Reactive Intermediates

Abstract

Electrosynthesis is undergoing a renaissance, but it is still far from being considered a standard method within the Chemists' synthetic toolbox. In this article, we will demystify organic electrochemistry by reviewing some practical methodologies developed in our laboratory to prepare highly reactive synthetic intermediates.

Current and Emerging Electrochemical Approaches for Chemical Manufacturing

“…Significant research activity in the last decade has occurred in the field of electro-organic syntheses with applications in fine chemicals and pharmaceuticals. [19][20][21][22][23] The activity has been driven by progress on multiple fronts: (i) the ability to access chemistries that through traditional synthetic means are difficult, hazardous, or highly waste generating, and (ii) the development of enabling technologies for non-electrochemists such as the IKA Electrasyn systems that provide "plug and play" reactions in standardized vials on a stir plate without the need for a potentiostat paired with recent tutorials geared toward organic chemists. [24][25][26] Electro-organic reactions can be used in coupling reactions such as with C-C and C-N bond formations, functionalization with heteroatoms, selective deprotections of functional groups, reduction of double bonds, hydrogenations, and many more that are of importance for the organic chemist's toolbox.…”

Electrochemically enabled oxidative aromatization of pyrazolines

“…Electrochemistry aligns with these principles of green chemistry, as hazardous and often expensive redox reagents can be substituted with electric current. 27 This also facilitates inherently safe processes, allowing for precise control over the reaction as the electron transfer is initially constrained to the electrode surface. 28 In addition, the generation of reagent waste can be minimized as solvents and supporting electrolytes can be recycled.…”

Electrochemical Isothiocyanation of Primary Amines

“…Electrochemistry opens the door to new chemical transformations by using electricity as one of the cheapest reagents. − Zhang and co-workers have recently disclosed an electrochemical isothiocyanation of alkylbenzene derivatives, yet the transformation is restricted to benzylic positions and uses a significant amount of wasteful supporting electrolyte . Herein, we describe a new general, practical, and supporting electrolyte-free electrochemical conversion of primary amines into isothiocyanates (Figure ).…”