Cyclization of Diazoacetamides Catalyzed by N-Heterocyclic Carbene Dirhodium(II) Complexes

Luis F. R. Gomes, Alexandre F. Trindade, Nuno R. Candeias, Luis F. Veiros, Pedro M. P. Gois, Carlos A. M. Afonso

Research output: Contribution to journalArticleScientificpeer-review

22 Citations (Scopus)

Abstract

The axial coordination of N-heterocyclic carbene ligands onto dirhodium(II) complexes was examined, together with its role in the intramolecular C-H insertion reactions of alpha-diazoacetamides. The formation of a decarbonylated product occurs by a free-carbene mechanism in which the structures of the catalyst and the acetamide play a decisive role.

Original languageEnglish
Pages (from-to)3519-3526
Number of pages8
JournalSynthesis: Stuttgart
Issue number20
DOIs
Publication statusPublished - 16 Oct 2009
Externally publishedYes
Publication typeA1 Journal article-refereed

Funding

We thank to Fundacao para a Ciencia a Tecnologia (POCI 2010) and FEDER (PTDC/QUI/66695/2006, PTDC/QUI/66015/2006, SFH/BPD/46589/2008 and SFRH/BD/30619/2006) for their financial support, and the Portuguese NMR Network (IST-UTL Center) for providing access to the NMR facility.

Keywords

  • carbenoids
  • carbene complexes
  • catalysis
  • diazo compounds
  • rhodium
  • C-H INSERTION
  • CHIRAL LEWIS-ACID
  • CAPROLACTAMATE
  • AMINATION
  • STEREOCONTROL
  • CARBOXYLATES
  • OXIDATION
  • ALDEHYDES
  • LACTAMS

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