C–H fluorination promoted by pyridine N-oxyl radicals

Abstract

Inspired by C–H hydroxylation by cytochrome P450 enzymes (P450s), we report here a method for preparing organofluorides through a single-electron transfer (SET) process, in which the pyridine N-oxyl radical greatly promotes the C–H fluorination. This reaction can be carried out in pure water at room temperature and accommodates a wide range of substrates, including bioactive molecules, with good yields. Mechanistic investigations indicate that reactions advance through radical intermediates.