Electrocatalytic Micelle-Driven Hydrodefluorination for Accessing Unprotected Monofluorinated Indoles

Abstract

Toxic organic solvents and electrolytes, traditionally indispensable for electro-organic synthesis, are now being reconsidered. In developing more sustainable electro-organic synthesis, we’ve harnessed the aqueous micelles as solvents and electrolyte-like structures when deformed under an electric field. The technology is showcased in synthetically highly valued hydrodefluorination reactions of difluorinated indoles. This mild electrosynthetic method produces monofluorinated unprotected indole scaffolds. Our approach minimizes waste and enhances atom economy, reducing reliance on expensive and hazardous solvents and electrolytes. The surfactant’s potential for recycling was verified for two cycles. Cyclic voltammetry analysis has corroborated that PS-750-M micelles in water establish a more efficient platform for hydrodefluorination. Our technology simplifies the production of monofluorinated indoles, which are crucial for many drug-like molecules.