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.