Organic Letters · 2020 · 45 citations · 80 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryAcid-base CatalysisCarboxylic AcidsCarboxylic DerivativesCatalytic MechanismsCross-coupling ReactionsReaction MechanismsAcid ChloridesChemoselective Bond CleavageCross-coupling CatalysisCross-electrophile CouplingKetonesNickel-catalyzed Cross-couplingRadical SpeciesSelective Bond Cleavage
The electrophile-electrophile cross-coupling of carboxylic acid derivatives and alkylpyridinium salts via C-N bond cleavage is developed. The method is distinguished by its simplicity and steers us through a variety of functionalized ketones in good to excellent yields. Besides acid chlorides, carboxylic acids were also employed as acylating agents, which enabled us to incorporate acid-sensitive functional groups such as MOM, BOC, and acetal. Control experiments with TEMPO revealed a radical pathway.
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N-methoxy-n-methylamides as effective acylating agents
Steven Nahm, Steven M. Weinreb · Tetrahedron Letters · 1981 · 1.8K citations
Reductive Cross‐Coupling Reactions between Two Electrophiles
Christiane E. I. Knappke, Sabine Grupe, Dominik Gärtner et al. · Chemistry - A European Journal · 2014 · 750 citations · Full text