Iron catalysts with N-ligands for carbene transfer of diazo reagents

Transition-metal-catalyzed carbene transfer reactions, involving diazo compounds and their precursors, are powerful tools for creating new C-C bonds. Depending on the involved catalytic system, the carbene insertion can efficiently be driven towards a specific functional group for the synthesis of a...

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Bibliographic Details
Published in:Chemical Society reviews 2020-07, Vol.49 (14), p.4867-495
Main Authors: Damiano, Caterina, Sonzini, Paolo, Gallo, Emma
Format: Article
Language:English
Subjects:
Biocatalysts
Catalysts
Catalytic activity
Chemical reactions
Coordination compounds
Covalent bonds
Fine chemicals
Functional groups
Germanium
Iron
Reaction mechanisms
Reagents
Silicon
Tin
Transition metals
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Summary:Transition-metal-catalyzed carbene transfer reactions, involving diazo compounds and their precursors, are powerful tools for creating new C-C bonds. Depending on the involved catalytic system, the carbene insertion can efficiently be driven towards a specific functional group for the synthesis of a wide portfolio of fine chemicals. The present report is focused on the catalytic activity of iron catalysts in promoting alkene cyclopropanations, C-H and X-H (X = N, O, S, Se, Si, Sn, Ge) functionalizations. Porphyrin, porphyrinoid and non-heme iron complexes are discussed by analyzing experimental studies and theoretical calculations performed for proposing reaction mechanisms. The catalytic activity of artificial iron biocatalysts is also briefly reported in order to underline the similarities and differences between reaction mechanisms mediated by modified biocatalysts and synthetic catalysts. This review summarizes the achievements made in this field since 2006. This review provides an overview of the catalytic activity of iron complexes of nitrogen ligands in driving carbene transfers towards C&z.dbd;C, C-H and X-H bonds. The reactivity of diazo reagents is discussed as well as the proposed reaction mechanisms.
ISSN:0306-0012
1460-4744
DOI:10.1039/d0cs00221f