RESUMEN
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.
RESUMEN
Benzylamines belong to an important class of building blocks in the synthesis of biologically active natural products and drugs. Encumbered by amide-directed ortho-C-H activation, remote para-selective C-H functionalization of benzylamines has hitherto not been realized to date. Here, we report a palladium-catalyzed para-selective C-H olefination and acetoxylation of benzylamines using a functionalized benzoyl template. Enhancing the coordination strength of the directing group in the template significantly improved the site selectivity of C-H functionalization.