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

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.