Gold(I)-Catalyzed Reactions between 2-(1-Alkynyl)-2-alken-1-ones and Vinyldiazo Ketones for Divergent Synthesis of Nonsymmetric Heteroaryl-Substituted Triarylmethanes: <i>N-</i> versus <i>C</i>-Attack Paths
Rahul Dadabhau Kardile, Rai‐Shung Liu
Abstract
Gold-catalyzed synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes using 2-(1-alkynyl)-2-alken-1-ones and vinyldiazo ketones is described. In this catalytic sequence, vinyldiazo ketones attack gold-containing 3-furylbenzyl cations to form the observed C(1)-addition products. We also note that vinyldiazo ketones can be thermally cyclized to yield pyrazole derivatives, which can react with 3-furylbenzyl cations to afford pyrazole-containing triarylmethanes, corresponding to a N(5)-addition path.
Topics & Concepts
ChemistryYield (engineering)CatalysisPyrazoleMedicinal chemistryCombinatorial chemistryOrganic chemistryMetallurgyMaterials scienceCatalytic Alkyne ReactionsCyclopropane Reaction MechanismsCatalytic C–H Functionalization Methods