title: 3-Alkylperoxy-3-cyano-oxindoles from 2-Cyano-2-diazo-N-phenyl-acetamides via Cyclizing Carbene Insertion and Subsequent Radical Oxidation.
abstract: A transition-metal-free one-pot sequence for the synthesis of 3-peroxy-substituted oxindoles from readily prepared 2-cyano-2-diazo-acetamides is reported. The two-step tandem process includes a highly efficient thermal intramolecular C-H-carbene insertion followed by a tetrabutylammonium iodide (TBAI) catalyzed radical C3-peroxy-functionalization. The protocol provides easy access to a new class of 3-cyano-3-peroxy-disubstituted oxindoles. Useful transformations to amides and alcohols are demonstrated.
authors.affiliation: Institute of Organic Chemistry, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Marvin
authors.initials: M
authors.lastname: Kischkewitz
authors.affiliation: Institute of Organic Chemistry, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Constantin-Gabriel
authors.initials: CG
authors.lastname: Daniliuc
authors.affiliation: Institute of Organic Chemistry, Westfälische Wilhelms-Universität , Corrensstraße 40, 48149 Münster, Germany.
authors.forename: Armido
authors.initials: A
authors.lastname: Studer