Helvetica Chimica Acta · 2012 · 13 citations · 9 references
Natural SciencesChemistryCatalysisOrganic ChemistryPhysical ChemistryCarboxylic AcidsCarboxylic DerivativesOrganic AcidsReaction MechanismsCarboxylic Acid Derivative SynthesisCarboxylic Acid Synthesis
Abstract A hydrogen chloride‐free variation of the Pinner reaction was developed, in which alcohols react with carbonitriles to furnish carboxylates. Best results were achieved with aliphatic alcohols, and aliphatic or benzylic nitriles in the presence of 2 equiv. of trimethylsilyl triflate (Me 3 SiOTf). With these substrates, yields exceeding 80% were achieved. A strictly neutral variation of this protocol is possible, when 1 equiv. of Et 3 N is added to the reaction mixture.
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