Hydrido-Cobalt Complexes for the Chemo- and Regioselective 1,2-Silylative Dearomatization of <i>N</i>-Heteroarenes
Cassandre C. Bories, Geoffrey Gontard, Marion Barbazanges, Étienne Derat, Marc Petit
Abstract
We describe an efficient regio- and chemoselective dearomatization of N -heteroarenes using hydrido-cobalt catalysts. Reactions were performed under mild conditions on a wide range of N -heteroarenes leading exclusively to the silyl-1,2-dihydroheteroarene. Various quinolines and pyridines bearing electron-donating and electron-withdrawing substituents are compatible with this methodology. DFT calculations, NMR spectroscopic studies, and X-ray diffraction analysis underlined the importance of a second silane for the final step of the reaction.
Topics & Concepts
RegioselectivityChemistryCobaltSilylationSilaneCatalysisMedicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsOrganoboron and organosilicon chemistry