Journal of the American Chemical Society · 2018 · 225 citations · 24 references
Natural SciencesChemistryMedicinal ChemistryGreen ChemistryOrganic ChemistrySynthetic Medicinal ChemistryCarboxylic AcidsCarboxylic DerivativesHeterocycle SynthesisLate-stage FunctionalizationAliphatic Carboxylic AcidsCarboxylic Acid Derivative SynthesisCarboxylic Acid SynthesisCopper CatalysisDecarboxylative CouplingLate-stage Functionalization Via Cross-couplingMedicinal Chemistry ApplicationsPhotoredox Cross-coupling
Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.
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The Many Roles for Fluorine in Medicinal Chemistry
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Catalytic alkylation of remote C–H bonds enabled by proton-coupled electron transfer
Gilbert J. Choi, Qilei Zhu, David C. Miller et al. · Nature · 2016 · 770 citations · Full text