Synthesis of Allenes by Hydroalkylation of 1,3-Enynes with Ketones Enabled by Cooperative Catalysis
Maxwell Eaton, Yuping Dai, Ziyong Wang, Bo Li, Walid Lamine, Karinne Miqueu, Shih‐Yuan Liu
Abstract
A method for the synthesis of allenes by the addition of ketones to 1,3-enynes by cooperative Pd(0)Senphos/B(C 6 F 5 ) 3 /NR 3 catalysis is described. A wide range of aryl- and aliphatic ketones undergo addition to various 1,3-enynes in high yields at room temperature. Mechanistic investigations revealed a rate-determining outer-sphere proton transfer mechanism, which was corroborated by DFT calculations.
Topics & Concepts
ChemistryCatalysisMechanism (biology)ArylCombinatorial chemistryProtonStereochemistryOrganic chemistryComputational chemistryPhilosophyEpistemologyAlkylPhysicsQuantum mechanicsCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Alkyne Reactions