Electrochemical Deoxygenative Silylation of Alcohols
Piret Villo, Malin Lill, Ziwei Fan, Kevin Breitwieser, J.M. White, Sergio Pérez Morente, Mårten S. G. Ahlquist, Helena Lundberg
Abstract
Alcohols are highly common organic compounds but remain scarce as alkyl donors in synthetic procedures. Here, we describe an electrochemical procedure for their deoxygenative cross-electrophile coupling with hydrosilanes, furnishing organosilane products in good to excellent yields. Mechanistic studies provide insights into the operating pathways of this semi-paired electrolytic transformation, suggesting that silyl ethers are likely reaction intermediates. Furthermore, a unified mechanistic proposal is presented that accounts for observed reactivity differences with analogous deoxygenative electrocarboxylation.
Topics & Concepts
SilylationAlkylElectrophileElectrochemistryChemistryReactivity (psychology)Combinatorial chemistryOrganic chemistryElectrolyteCatalysisElectrodeMedicinePhysical chemistryAlternative medicinePathologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques