Hydrosilane-Mediated Electrochemical Reduction of Amides
Kazuhiro Okamoto, Shingo Nagahara, Yasushi Imada, Risako Narita, Yoshikazu Kitano, Kazuhiro Chiba
Abstract
Electrochemical reduction of amides was achieved by using a hydrosilane without any toxic or expensive metals. The key reactive ketyl radical intermediate was generated by cathodic reduction. Continuous reaction with anodically generated silyl radicals or zinc bromide resulted in chemoselective deoxygenation to give the corresponding amines.
Topics & Concepts
ChemistryDeoxygenationKetylTributyltin hydrideElectrochemistryRadicalCathodic protectionBromideSilylationZincZinc bromideCombinatorial chemistryPhotochemistryInorganic chemistryOrganic chemistryElectrodeCatalysisPhysical chemistryRadical Photochemical ReactionsAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization Methods