Palladium-Catalyzed Semihydrogenation of Alkynes with EtOH: Highly Stereoselective Synthesis of E- and Z-Alkenes
Chengniu Wang, Jin Dong, Dawei Xu, Tingting Li, Xi Zhao
Abstract
Abstract A palladium-catalyzed semihydrogenation of alkynes to E- and Z-alkenes employing EtOH as the hydrogenating agent is reported. The selectivity of the reaction system was effectively controlled by ligand/additive and solvent regulation. The use of sodium acetate/triethanolamine (NaOAc/TEOA), THF, and (1R,2R)-bis[(2-methoxyphenyl)phenylphosphino]ethane [(R,R)-DIPAMP] in CH3CN was critical for the stereoselective semihydrogenation of alkynes. The general applicability of this procedure was highlighted by the synthesis of more than 36 alkenes, in good yields with high stereoselectivities.
Topics & Concepts
ChemistryStereoselectivityPalladiumTriethanolamineCatalysisSelectivitySolventLigand (biochemistry)Combinatorial chemistryOrganic chemistryMedicinal chemistryReceptorBiochemistryAnalytical Chemistry (journal)Asymmetric Hydrogenation and CatalysisCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions