Intramolecular C-H insertion catalyzed by dirhodium(II) complexes using CO2 as the reaction media

Malgorzata E. Zakrzewska, Pedro M. S. D. Cal, Nuno R. Candeias, Rafal Bogel-Lukasik, Carlos A. M. Afonso, Manuel N. Ponte, Pedro M. P. Gois

    Research output: Contribution to journalArticleScientificpeer-review

    15 Citations (Scopus)

    Abstract

    In this work, the intramolecular C-H insertion of diazoacetamides catalyzed by dirhodium(II) complexes and using CO2 as solvent is disclosed. The expected lactams were obtained in yields over 97%. The asymmetric intramolecular C-H insertion was also achieved and the beta-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 - 2012
    Publication typeA1 Journal article-refereed

    Funding

    We thank the Fundacaopara a Ciencia e Tecnologia (POCI 2010) and FEDER (SFRH/BPD/46589/2008, SFRH/BD/72376/2010 PTDC/QUI/66695/2006, PTDC/QUI/70383/2006) for financial support.

    Keywords

    • diazoacetamides
    • C-H insertion
    • dirhodium(II)
    • lactams
    • scCO(2)
    • ASYMMETRIC CYCLOPROPANATION
    • ALPHA-DIAZOACETAMIDES
    • HOMOGENEOUS CATALYSIS
    • SUPERCRITICAL FLUIDS
    • CARBOXYLATES
    • ENANTIOSELECTIVITY
    • TRANSFORMATIONS
    • IMMOBILIZATION
    • ACTIVATION
    • STRATEGY

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