Organic Letters · 2022 · 26 citations · 38 references
Natural SciencesChemistryCatalysisElectrochemistryOrganic ChemistryCatalytic MechanismsCross-coupling ReactionsElectrochemical SynthesisOrganic SynthesisRadical ReactionsRedox CatalysisCathodic ReductionCathodic Reduction ProcessesControl ExperimentsKetonesRegioselectivityScale-up Experiments
A regioselective coupling of aliphatic ketones with alkenes has been realized by cathodic reduction. This reaction enables the formation of ketyl radicals and the activation of challenging alkenes under mild electrolysis conditions, providing an effective protocol for accessing diverse tertiary alcohols with substrate-dependent regioselectivity. The practicability of this reaction is demonstrated by scale-up experiments. The hydrogen source for the products, the migration isomerization of allylarenes, and the applicability of internal alkenes are demonstrated by control experiments.
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Copper-catalyzed asymmetric addition of olefin-derived nucleophiles to ketones
Yang Yang, Ian B. Perry, Gang Lü et al. · Science · 2016 · 298 citations