Organic Electrosynthesis has long been a useful synthetic tool, with examples as early as 1832. However, the need for specialist equipment, alongside issues with reproducibility have hindered method development. With the introduction of commercially available standardised equipment such as the IKA Electrasyn 2.0 and its accessories, electrosynthesis has experienced a resurgence in interest, and has proven to be a valuable and versatile tool in both small- and industrial-scale chemical synthesis. Previously, we reported the use of electrogenerated aroyloxy radicals, formed via anodic oxidation of aromatic carboxylic acids, to synthesise a library of functionalised phthalides under mild and green conditions. We have now extended this methodology towards the use of aliphatic carboxylic co-acids as a cheap and readily available source of alkyl radicals, which readily undergo an unusual metal-free sp3-sp3 cross coupling in solution. The exceptional versatility of our new methodology is exemplified through our successful synthesis of functionalised lactones, which are of great interest due to their fungicidal, antibiotic, and anti-cancer properties, under mild and ecologically friendly conditions. Moreover, using similar conditions, it has been possible to synthesise a library of functionalised orthoesters, which are highly versatile and reactive compounds with uses in medicinal and material chemistry, thus circumventing the use of traditional methods which rely on dangerous and toxic reagents, and have no scope for derivatisation. A summary of our recent results will be presented.

Electrosynthesis: A practical and versatile method for small molecule synthesis

ACS Fall 2020 Virtual Meeting

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