Iron‐Catalyzed Intermolecular Functionalization of Non‐Activated Aliphatic C−H Bonds via Carbene Transfer

The modification of strong Csp3−H bonds via iron carbene intermediates under mild reaction conditions has been an important challenge with attractive prospective in organic synthesis. In this work, we show the efficient combination of an electrophilic iron catalyst with a lithium Lewis acid for the...

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Veröffentlicht in:Advanced synthesis & catalysis 2020-11, Vol.362 (22), p.5116-5123
Hauptverfasser: Rodríguez, Mònica, Font, Gemma, Nadal‐Moradell, Joel, Hernán‐Gómez, Alberto, Costas, Miquel
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Sprache:eng
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Zusammenfassung:The modification of strong Csp3−H bonds via iron carbene intermediates under mild reaction conditions has been an important challenge with attractive prospective in organic synthesis. In this work, we show the efficient combination of an electrophilic iron catalyst with a lithium Lewis acid for the functionalization of strong Csp3−H bonds of cyclic and linear alkanes by the activation of commercially available ethyl diazoacetate (EDA). The reaction proceeds with good yields, under mild reaction conditions (40 °C) and large excess of substrate is not needed. In addition, excellent activity is observed in the cyclopropanation of challenging aliphatic olefins.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000817