Angewandte Chemie · 2017 · 26 citations · 54 references
Natural SciencesChemical EngineeringChemistryCatalysisElectrochemistryOrganic ChemistryCatalyst DesignCatalytic MechanismsCross-coupling ReactionsOrganic SynthesisRedox CatalysisBrønsted Acid CatalysisBrønsted AcidityCatalytic Reaction MechanismsFrustrated Lewis PairsHybrid CatalysisLewis Acid CatalysisReduction CatalysisReductive Cross-coupling
Abstract Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H 2 , R‐OH or H 2 O generates the required Brønsted acid in a reversible, “turn on” manner. The method is not only a complementary metal‐free reductive etherification, but also a niche procedure for ethers that would be either synthetically inconvenient or even intractable to access by alternative synthetic protocols.
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Reversible, Metal-Free Hydrogen Activation
Gregory C. Welch, Ronan R. San Juan, Jason D. Masuda et al. · Science · 2006 · 2.1K citations
Douglas W. Stephan · Journal of the American Chemical Society · 2015 · 1.2K citations
Frustrated Lewis Pairs: From Concept to Catalysis
Douglas W. Stephan · Accounts of Chemical Research · 2014 · 1.1K citations