4.2 Article

On the formation of seven-membered rings by arene-ynamide cyclization

Journal

MONATSHEFTE FUR CHEMIE
Volume 150, Issue 1, Pages 3-10

Publisher

SPRINGER WIEN
DOI: 10.1007/s00706-018-2320-x

Keywords

Heterocycles; Strained molecules; BrOnsted acid; Catalysis

Funding

  1. Austrian Science Fund (FWF)
  2. ERC (CoG VINCAT)
  3. FWF [P30226]
  4. University of Vienna

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A BrOnsted acid-catalyzed selective arene-ynamide cyclization is described. This reaction proceeds via a keteniminium intermediate and enables the preparation of seven-membered ring enamide products. Mechanistic studies uncover an unusual product inhibition behavior. [GRAPHICS] .

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