Practical heptafluoroisopropylation of nitrogen-containing (hetero)aromatics under visible light

Abstract

A practical visible-light-driven heptafluoroisopropylation of substituted anilines and heterocyclic aromatics has been achieved. The key to the success of this facile transformation lies in the in-situ generation of a novel electron donor-acceptor (EDA) complex between trimethyl phosphite and heptafluoroisopropyl iodide, which enables the formation of diverse heptafluoroisopropylated products in a regio-selective fashion under mild reaction conditions. In addition, the present EDA protocol demonstrates applicability for other perfluoroalkylation reactions. This work features high site-selectivity, transition-metal and photosensitizer free conditions, and broad substrate scope, constituting a greener alternative to access the synthetically important perfluoroalkyl-containing molecules, such as Broflanilide.