Ni<sup>0</sup>-Catalyzed Regioselective [2 + 2 + 2] Cyclotrimerization of 1,3-Diynes: An Expeditious Synthesis of Hexasubstituted Alkynyl Benzenes
Rajesh Chakrabortty, Suman Ghosh, Venkataraman Ganesh
Abstract
In the present work, we demonstrate a regioselective [2 + 2 + 2] cyclotrimerization of 1,3-diynes catalyzed by Ni 0 to provide hexasubstituted benzenes (HSBs). HSBs have significant applications as functional materials and pharmaceuticals. The present protocol exhibited remarkable versatility, transforming 1,3-diynes with diverse alkyl, aryl, and heterocyclic groups to the corresponding HSBs. With the help of control experiments and density functional theory (DFT), the mechanism of the reaction and the origin of regioselectivity were elucidated.
Topics & Concepts
RegioselectivityChemistryCatalysisArylAlkylDensity functional theoryMedicinal chemistryCombinatorial chemistryOrganic chemistryComputational chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms