Metal-Free Fluoro-Benzoxazepine Synthesis

  • ChemPubSoc Europe Logo
  • Author: David Smith
  • Published Date: 04 February 2016
  • Source / Publisher: Chemistry - A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
thumbnail image: Metal-Free Fluoro-Benzoxazepine Synthesis

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Fluorinated organic compounds are of great interest to any number of fields of chemistry, including pharmaceutical and agrochemical industry, non-invasive diagnosis, and development of "intelligent" materials. The presence of a fluorine atom can have a significant impact on a molecule’s solubility, bioavailability, and stability.

Tanja Gulder and co-workers at TU Munich in Germany have reported the synthesis of the pharmacologically interesting heterocycles 4-fluoro-1,3-benzoxazepines from o-styryl benzamides by using a fluorination/aryl Migration/cyclization cascade strategy. Notably, Gulder’s synthesis avoid the need for transition metal catalysts, instead using a bench-stable hypervalent fluoro iodane reagent as an electrophilic source of fluorine. This reagent is not only significantly more reactive than the well-established iodine(III)-based fluorinating reagent Selectfluor, but provides completely different chemoselectivity, providing seven-membered ring benzoxazepines instead of oxazines. Moreover, this strategy is used in the synthesis of 20 structurally distinct congeners and proceeds with complete regioselectivity under mild reaction conditions.


 

This article is soon to feature in Chemistry ‒ A European Journal's up-coming "Women in Chemistry" special issue.

 

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