Organic Letters · 2017 · 93 citations · 56 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCarboxylic AcidsCarboxylic DerivativesCatalytic MechanismsCross-coupling ReactionsDiversity-oriented SynthesisPhotocatalysisActivation Of Carboxylic AcidsAliphatic Carboxylic AcidsCross CouplingCross-coupling CatalysisKetonesNickel-catalyzed Cross-couplingPhotoredox CatalysisTransition-metal-catalyzed Cross-coupling
bond formation based on the direct conversion of carboxylic acids has been established. This protocol is enabled by the synergistic, Ir-photoredox/nickel catalytic cross-coupling of in situ activated carboxylic acids and alkyltrifluoroborates. This versatile method is amenable to the cross-coupling of structurally diverse carboxylic acids with various potassium alkyltrifluoroborates, affording the corresponding ketones with high yields. In this operationally simple cross-coupling protocol, aliphatic ketones are obtained in one step from bench stable, readily available carboxylic acids.
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