title: Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers.
abstract: An iron-catalyzed coupling reaction of O-acyloximes and O-benzoyl amidoximes with silyl enol ethers is reported. The protocol provides access to functionalized pyrroles, 1,6-ketonitriles, pyrrolines and imidazolines via carbon-centered radicals generated from an initially formed iminyl radical. The intramolecular cyclization and ring-opening processes of the iminyl radical take place preferentially over reactions that proceed through a 1,3-hydrogen transfer, providing insights into iron-catalyzed reactions with oxime derivatives. The cheap and environmentally friendly iron catalyst, the broad substrate scope and the functional group compatibility make this protocol useful for synthesis of valuable nitrogen-containing products.
authors.affiliation: Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, 106 91, Stockholm, Sweden.
authors.forename: Hai-Bin
authors.identifier: http://orcid.org/0000-0002-8977-4963
authors.initials: HB
authors.lastname: Yang
authors.affiliation: Department of Organic Chemistry, Stockholm University, Arrhenius Laboratory, 106 91, Stockholm, Sweden.
authors.forename: Nicklas
authors.identifier: http://orcid.org/0000-0002-9085-0476
authors.initials: N
authors.lastname: Selander
keywords: acyloximes; iron; pyrroles; radicals; silyl enol ethers