Molecular Editing of Toluene by Sequential meta-C–H/Benzylic C–N Deaminative Functionalizations

Abstract

An approach to synthesizing structurally diverse toluene derivatives via sequential meta-C−H and benzylic C−N deaminative functionalization was developed by using a recyclable bifunctional directing template. The functionalized Katritzky salt intermediates are shown to be engaged in a wide range of carbon−carbon and carbon−heteroatom bond formation reactions. The synthetic utility of the strategy was demonstrated by late-stage functionalization of toloxatone.