Rh(II)-catalyzed intramolecular C-H insertion of diazo substrates in water: Scope and limitations

Nuno R. Candeias, Pedro M. P. Gois, Carlos A. M. Afonso

Research output: Contribution to journalArticleScientificpeer-review

97 Citations (Scopus)

Abstract

Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from R-diazo-acetamides can be achieved in water by using an appropriate combination of the catalyst and amide groups, which creates a larger hydrophobic environment around the reactive carbenoid center.

Original languageEnglish
Pages (from-to)5489-5497
Number of pages9
JournalJournal of Organic Chemistry
Volume71
Issue number15
DOIs
Publication statusPublished - 21 Jul 2006
Externally publishedYes
Publication typeA1 Journal article-refereed

Keywords

  • RHODIUM(II) CATALYZED-REACTIONS
  • ORGANIC-REACTIONS
  • ALPHA-DIAZOACETAMIDES
  • N-ARYLDIAZOAMIDES
  • YLIDE FORMATION
  • DIRHODIUM(II)
  • CARBENOIDS
  • CYCLOPROPANATION
  • SOLVENT
  • ENANTIOSELECTIVITY

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