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

The modification of strong Csp(3)-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 th...

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Detalhes bibliográficos
Autores: Rodríguez, Mónica, Font, Gemma, Nadal Moradell, Joel, Hernán-Gómez Robledo, Alberto|||0000-0001-7020-0196, Costas, Miquel
Formato: artículo
Fecha de publicación:2020
País:España
Recursos:Universidad de Alcalá (UAH)
Repositorio:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:inglés
OAI Identifier:oai:ebuah.uah.es:10017/64265
Acesso em linha:http://hdl.handle.net/10017/64265
https://dx.doi.org/10.1002/adsc.202000817
Access Level:acceso abierto
Palavra-chave:C-H functionalization
C-C bond formation
Carbene transfer
Iron catalyst
Diazo compounds
Química
Chemistry
Descrição
Resumo:The modification of strong Csp(3)-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 Csp(3)-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 degrees C) and large excess of substrate is not needed. In addition, excellent activity is observed in the cyclopropanation of challenging aliphatic olefins.