Site-Selective Modification of Peptides via Late-Stage Pd-Catalyzed Tandem Reaction of Phenylalanine with Benzoquinone
Jian Tang, Fengjie Lu, Yujie Geng, Yanxia Liu, Ensheng Zhang
Abstract
An efficient and straightforward approach for site-selective functionalization of phenylalanine and phenylalanine-containing peptide via a Pd-catalyzed tandem reaction has been developed. The robust method underwent dual C-H activation, including C-C coupling with benzoquinone and intramolecular C-N cyclization, providing a feasible and rapid synthetic route to incorporate 4-benzoquinone-indoline fragments into peptides.
Topics & Concepts
ChemistryTandemCatalysisPhenylalanineBenzoquinoneCombinatorial chemistryPalladiumStereochemistryOrganic chemistryBiochemistryAmino acidMaterials scienceComposite materialChemical Synthesis and AnalysisCatalytic C–H Functionalization MethodsClick Chemistry and Applications