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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 21
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Original Articles

Bismuth Triflate–Catalyzed Friedel–Crafts Acylations of Sydnones

, &
Pages 3220-3229 | Received 11 Mar 2011, Published online: 17 Aug 2012
 

Abstract

Friedel–Crafts acylations of various 3-arylsydnones at the C4 position have been achieved in good yields using 4 equivalents of an alkyl anhydride and 25 mol% each of bismuth triflate and lithium perchlorate in anhydrous acetonitrile at 95 °C. Acylations appear to be faster with arylsydnones bearing electron-donating moieties and sterically unencumbered anhydrides.

GRAPHICAL ABSTRACT

Notes

a The Bi(OTf)3 in these studies was freshly prepared from triphenyl bismuthene.

b Unrecrystallized yield.

a An additional equivalent of acetic anhydride and 10 mol % of Bi(OTf)3/LiClO4 were added after 26 h.

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