Cu-Catalyzed C–H Allylation of Benzimidazoles with Allenes
Yaxi Dong, Bernhard Breit
Abstract
CuH-catalyzed intramolecular cyclization and intermolecular allylation of benzimidazoles with allenes have been described. The reaction proceeded smoothly with the catalytic system of Cu(OAc)2/Xantphos and catalytic amount of (MeO)2MeSiH. This protocol features mild reaction conditions and a good tolerance of substrates bearing electron-withdrawing, electron-donating, or electron-neutral groups. A new catalytic mechanism was proposed for this copper hydride catalytic system.
Topics & Concepts
ChemistryCatalysisXantphosIntramolecular forceIntermolecular forceAlleneMedicinal chemistryCopperMarkovnikov's ruleCatalytic cycleCombinatorial chemistryOrganic chemistryMoleculePalladiumRegioselectivityCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques