Ligand effects in the metal catalysed reactions of N-aryldiazoamides: Ylide formation vs. insertion reactions

C J Moody, S Miah, A M Z Slawin, D J Mansfield, I C Richards

Research output: Contribution to journalArticlepeer-review

40 Citations (Scopus)

Abstract

Diazoamides 1a and 1b were prepared from 2-(O-allyl)- and 2-(S-allyl) anilines 2 respectively. Copper(II) catalysed decomposition of 1 resulted in formation of benzofused heterocycles 7 by [2,3]-rearrangement of the intermediate ylide. Rhodium(II) perfluorbutyramide catalysed reaction, however, gave mainly the indoles 8, 9 whereas rhodium(II) acetate catalysed reaction resulted in a mixture of products, with p-lactams formed by intramolecular C-H insertion predominating. Catalysed decomposition of N-pyridyl diazoamide 13 gave the stable pyridinium ylide 14, (C) 1998 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)9689-9700
Number of pages12
JournalTetrahedron
Volume54
Issue number33
Publication statusPublished - 13 Aug 1998

Keywords

  • carbenes and carbenoids
  • ylides
  • catalysis
  • C-H INSERTION
  • CARBON-HYDROGEN INSERTION
  • ALPHA-DIAZOCARBONYL COMPOUNDS
  • RHODIUM(II) CARBOXYLATE
  • ORGANIC-SYNTHESIS
  • CYCLOPENTANE CONSTRUCTION
  • STEREOSELECTIVE SYNTHESIS
  • CYCLOADDITION REACTIONS
  • CARBENOID REACTIONS
  • DIAZO-COMPOUNDS

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