NHC-Catalyzed Formal [4 + 2] Annulation of <i>o</i>-Formyl-Tethered Michael Acceptors and Ynones to Access Highly Functionalized Naphthalene Derivatives
Jakkula Ramarao, M. RAMBABU, Surisetti Suresh
Abstract
Herein we demonstrate a novel organocatalytic method to access multifunctionalized naphthalenes via an NHC-catalyzed reaction of ynones and o -formyl-tethered Michael acceptors. The presented method proceeds through an intermolecular Stetter reaction–cyclization–aromatization cascade and represents a rare example of organocatalytic benzannulation for the synthesis of substituted arenes by using ynone as a two-carbon synthon. The current method has broad substrate scope; postsynthetic transformations and gram-scale syntheses highlight the practicality of the displayed methodology.
Topics & Concepts
ChemistryAnnulationNaphthaleneCatalysisMichael reactionMedicinal chemistryCombinatorial chemistryOrganic chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods