Synthetic Organic Electrochemistry in Deep Eutectic Solvents

Abstract

Electrochemistry is an increasingly well-known method of organic synthesis due to its sustainability and specific reaction manipulation capabilities. Organic electrochemical synthesis requires an electrolyte, or a salt, to facilitate charge transport in addition to a solvent. Both the electrolyte and the solvent are sources of waste in an organic reaction and thus contribute to its environmental impact. Deep Eutectic Solvents (DESs) are increasingly well-known recyclable liquids that contain salts as at least one of their components. This thesis project explores the use of DESs as organic electrochemical solvents for the first time. By performing various allylations of aldehydes using different DESs and electrode pairings and analyzing the yields of each round, reaction conditions are optimized. The recyclability of the DES is also explored. It is discovered that DESs are excellent solvents to use for electrochemical allylations because each 2 mL of DES can be reused at least three times, and other reaction components such as SnCl2 are easily regenerated for future use. The combination of electrochemistry and DESs yields a doubly green synthetic reaction that can be replicated in many large-scale settings, such as the pharmaceuticals industry. This process would minimize waste production and allow for reusable materials, saving both money and the environment. KEYWORDS: organic chemistry; chemistry; synthesis; electrochemistry; deep eutectic solvents