C–H Xanthylation: A Synthetic Platform for Alkane Functionalization
journal contributionposted on 14.10.2016, 13:03 by William L. Czaplyski, Christina G. Na, Erik J. Alexanian
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.