Catalytic C–C Cleavage/Alkyne–Carbonyl Metathesis Sequence of Cyclobutanones
Jiqiang Gao, Chunhui Liu, Zhongjuan Li, Haotian Liang, Yuhui Ao, Jinbo Zhao, Yuchao Wang, Yuanqi Wu, Yu Liu
Abstract
A ring-opening/alkyne–carbonyl metathesis sequence of alkyne-tethered cyclobutanones catalyzed by AgSbF6 is realized for the first time to furnish multisubstituted naphthyl ketones under mild conditions. A range of substrates decorated with various substituents at different positions were all well accommodated. Preliminary mechanistic studies show that silver salt acted as a Lewis acid to facilitate both C–C cleavage of the cyclobutanone moiety and the subsequent metathesis between C═O and C≡C bonds.
Topics & Concepts
ChemistryCleavage (geology)MetathesisCatalysisAlkyneSequence (biology)StereochemistrySalt metathesis reactionCombinatorial chemistryOrganic chemistryBiochemistryBiologyFracture (geology)PolymerizationPolymerPaleontologySynthetic Organic Chemistry MethodsCyclopropane Reaction MechanismsCatalytic Alkyne Reactions