AI Article Synopsis

  • A pentafluorophenylammonium triflate (PFPAT) catalyst (at 5 mol %) effectively facilitated the C-acylation process of enol silyl ethers with acid chlorides, yielding a range of beta-diketones with yields ranging from 62% to 92% (12 examples).
  • The catalyst also supported the C-acylation of ketene silyl acetals and ketene silyl thioacetals, leading to successful crossed Claisen condensation reactions.
  • This process produced both alpha-monoalkylated and less common alpha,alpha-dialkylated beta-keto (thio)esters, achieving good to excellent yields (38 examples;

Article Abstract

A pentafluorophenylammonium triflate (PFPAT) catalyst (5 mol %) successfully promoted C-acylation of enol silyl ethers with acid chloride to produce various beta-diketones (12 examples; 62-92% yield). Similarly, C-acylation of ketene silyl acetals or ketene silyl thioacetals (i.e., crossed Claisen condensation) proceeded smoothly to provide not only alpha-monoalkylated beta-keto (thio)esters but also thermodynamically unfavorable (less accessible) alpha,alpha-dialkylated beta-keto (thio)esters in good to excellent yield (38 examples; 60-92% yield).

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http://dx.doi.org/10.1021/ol070191bDOI Listing

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