Mild and Efficient Pentafluorophenylammonium Triflate (PFPAT)-Catalyzed C-Acylations of Enol Silyl Ethers or Ketene Silyl (Thio)Acetals with Acid Chlorides

Akira Iida, Jun Osada, Ryohei Nagase, Tomonori Misaki, and Yoo Tanabe*
Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
Org. Lett., 2007, 9 (10), pp 1859–1862
DOI: 10.1021/ol070191b
Publication Date (Web): April 13, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, tanabe@kwansei.ac.jp

Abstract

Abstract Image

A pentafluorophenylammonium triflate (PFPAT) catalyst (5 mol %) successfully promoted C-acylation of enol silyl ethers with acid chloride to produce various β-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 α-monoalkylated β-keto (thio)esters but also thermodynamically unfavorable (less accessible) α,α-dialkylated β-keto (thio)esters in good to excellent yield (38 examples; 60−92% yield).

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History

  • Published In Issue May 10, 2007
  • Received January 25, 2007

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