54497-82-4Relevant academic research and scientific papers
Direct Decarboxylative Functionalization of Carboxylic Acids via O-H Hydrogen Atom Transfer
Na, Christina G.,Ravelli, Davide,Alexanian, Erik J.
supporting information, p. 44 - 49 (2020/01/22)
Decarboxylative functionalization via hydrogen atom transfer offers an attractive alternative to standard redox approaches to this important class of transformations. Herein, we report a direct decarboxylative functionalization of aliphatic carboxylic acids using N-xanthylamides. The unique reactivity of amidyl radicals in hydrogen atom transfer enables decarboxylative xanthylation under redox-neutral conditions. This platform provides expedient access to a range of derivatives through subsequent elaboration of the xanthate group.
C-H Xanthylation: A Synthetic Platform for Alkane Functionalization
Czaplyski, William L.,Na, Christina G.,Alexanian, Erik J.
supporting information, p. 13854 - 13857 (2016/11/06)
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.
