Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO 2 as the reaction media

Małgorzata E. Zakrzewska, Pedro M.S.D. Cal, Nuno R. Candeias, Rafał Bogel-Łukasik, Carlos M. Afonso, Manuel N. Ponte, Pedro M.P. Gois

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO 2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the β-lactam 14 was obtained in >97% yield and 65% ee using the chiral dirhodium(II) catalyst Rh 2(S-PTTL) 4. Finally, the dirhodium(II) complex Rh 2(OAc) 4 was used in two consecutive cycles in which complete conversion to the lactam was observed.

Original languageEnglish
Pages (from-to)211-240
Number of pages30
JournalGreen Chemistry Letters and Reviews
Volume5
Issue number2
DOIs
Publication statusPublished - Jun 2012

Keywords

  • C-H insertion.
  • diazoacetamides.
  • dirhodium(II).
  • lactams.
  • scCO

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