Palladium-Catalyzed Tandem Dehydrogenative [4 + 2] Annulation of Terminal Olefins with <i>N</i>-Sulfonyl Amides via C–H Activations
Manman Sun, Weida Chen, Xiangyu Xia, Guodong Shen, Yongmin Ma, Jianguo Yang, Hanfeng Ding, Zhiming Wang
Abstract
A palladium-catalyzed tandem dehydrogenative [4 + 2] annulation of terminal olefins with N-sulfonyl amides via C(sp2)–H activation, allylic C(sp3)–H activation, and homoallylic C(sp3)–H elimination processes has been developed. Promoted by the DMSO ligand, various benzamides, heterocyclic arylamides, alkenyl carboxamides, and commercial olefins are found to be efficient substrates to construct important heterocyclic compounds bearing a vinyl substituent with high E stereoselectivity. Using air as the terminal oxidant also provides a great advantage regarding environmental friendliness.
Topics & Concepts
ChemistryAnnulationAllylic rearrangementSulfonylTandemCatalysisStereoselectivitySubstituentPalladiumLigand (biochemistry)Medicinal chemistryCombinatorial chemistryStereochemistryOrganic chemistryReceptorBiochemistryAlkylMaterials scienceComposite materialCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSulfur-Based Synthesis Techniques