Oxidative Difunctionalization of <i>N</i>-Aryl Bicyclobutyl Amides with Aldehydes: Divergent Synthesis of Acylated and Alkylated 3-Spirocyclobutyl Oxindoles
Pengfei Xia, Jiao Zhou, Jing Yuan, Rui Zeng, Yu Liu, Kewen Tang, Jian-Hong Fan
Abstract
An efficient and operationally simple oxidative radical difunctionalization of N -aryl bicyclobutyl (BCB) amides with aldehydes is described. It was found that acylated 3-spirocyclobutyl oxindoles were generated from the coupling of BCB-amides and aromatic aldehydes, while reactions gave exclusively decarbonylative alkylarylation products using alkyl aldehydes as radical precursors.
Topics & Concepts
ChemistryAlkylationArylOxidative phosphorylationCombinatorial chemistryOrganic chemistryBiochemistryCatalysisAlkylAsymmetric Synthesis and CatalysisChemical Synthesis and AnalysisAdvanced Synthetic Organic Chemistry