Selective radical-type perfluoro-tert-butylation of unsaturated compounds with a stable and scalable reagent

Abstract

Despite the promising potential of the perfluoro-tert-butyl group in diverse fields such as magnetic resonance imaging, material science and drug design, incorporating this group into organic molecules is still a formidable task, primarily due to its bulky structure and unique fluorine effect. Herein, we describe a stable and scalable reagent for radical-type perfluoro-tert-butylation, which is synthesized in large scale from commercial perfluoro-tert-butanol and a designed benzothiazole hypervalent iodonium salt. Highly E-selective photo-driven C(sp²)–H functionalization of styrene derivatives is achieved in a triplet-triplet energy transfer halted manner, while thermally disfavored Z-products are also accessible by removing the energy antagonist. The application of this method is further demonstrated by late-stage functionalization and divergent synthesis of perfluoro-tert-butylated compounds.