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Journal of the American Chemical Society

C-H Xanthylation: A Synthetic Platform for Alkane Functionalization.


PMID 27739673

Abstract

Intermolecular functionalizations of aliphatic C-H bonds offer unique strategies for the synthesis and late-stage derivatization of complex molecules, but the chemical space accessible remains limited. Herein, we report a transformation significantly expanding the chemotypes accessible via C-H functionalization. The C-H xanthylation proceeds in useful chemical yields with the substrate as the limiting reagent using blue LEDs and an easily prepared N-xanthylamide. The late-stage functionalizations of complex molecules occur with high levels of site selectivity, and a variety of common functionality is tolerated in the reaction. This approach capitalizes on the versatility of the xanthate functional group via both polar and radical manifolds to unlock a wide array of C-H transformations previously inaccessible in synthesis.