Facile Double-Lithiation of a Transient Urea: Vicarious ortho-Metalation of Aniline Derivatives

Chris E. Houlden, Guy C. Lloyd-Jones*, Kevin I. Booker-Milburn

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

A convenient one-pot method for the conversion of phenylisocyanate into ortho-functionalized aniline derivatives has been developed. The reaction proceeds via the selective ortho-metalation of a transient labile urea, which can be considered as a synthetic equivalent of 2-lithiophenylisocyanate, a highly improbable intermediate.

Original languageEnglish
Pages (from-to)3090-3092
Number of pages3
JournalOrganic letters
Volume12
Issue number13
DOIs
Publication statusPublished - 2 Jul 2010

Keywords / Materials (for Non-textual outputs)

  • DIRECTED ORTHO-METALATION
  • C-H ACTIVATION
  • DIRECT ARYLATION
  • BOND FORMATION
  • AMINES
  • N'-ARYL-N,N-DIMETHYLUREAS
  • FUNCTIONALIZATION
  • N,N'-DIARYLUREAS
  • CARBONYLATION
  • REARRANGEMENT

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