Copper-Catalyzed Annulation–Trifluoromethyl Functionalization of Enynones
Jia‐Yin Wang, Sai Zhang, Yao Tang, Shenghu Yan, Guigen Li
Abstract
The Cu(I)-catalyzed annulation–halotrifluoromethylation and cyanotrifluoromethylation of enynones have been established, enabling multibond formations of the synthesis of quaternary carbon-centered 1-indanones in moderate to good chemical yields. The reaction of enynones with Togni’s reagent and chloro- or bromotrimethylsilane afforded halo- and CF 3 -containing 1-indenones. However, the addition of K 3 PO 4 as a base into the catalytic system led to forming cyano-anchored ( Z )-1-indanones as major stereoisomeric products. This strategy exhibits remarkable compatibility with a wide range of enynones.
Topics & Concepts
ChemistryAnnulationReagentTrifluoromethylCatalysisQuaternary carbonCombinatorial chemistryCopperSurface modificationCompatibility (geochemistry)Reaction conditionsOrganic chemistryEnantioselective synthesisChemical engineeringPhysical chemistryEngineeringAlkylFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsInorganic Fluorides and Related Compounds