Access to 5-bromopentanal and 6-bromohexanal derivatives via the bromination/hydrolysis of C,O-bis-zirconocenes generated from unsaturated Weinreb amides

Org Biomol Chem. 2022 Jul 27;20(29):5803-5811. doi: 10.1039/d2ob01073a.

Abstract

Access to 5-bromopentanal and 6-bromohexanal derivatives from Weinreb amides is described. The method relies on the sequential C-bromination/zircona-aminal hydrolysis of bis-C,O-zirconocenes, which are generated in situ from unsaturated Weinreb amides using Schwartz's reagent. Synthetic illustrations of such bromo-aldehydes, which can act as carbocycle and heterocycle precursors, are also presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes
  • Amides*
  • Halogenation*
  • Hydrolysis
  • Organometallic Compounds
  • Zirconium

Substances

  • Aldehydes
  • Amides
  • Organometallic Compounds
  • Zirconocene dichloride
  • Zirconium