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Synthesis of Polycyclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA)

Antonio Arcadi, Giancarlo Fabrizi, Andrea Fochetti, Roberta Franzini, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Andrea Serraiocco

2021European Journal of Organic Chemistry16 citationsDOI

Abstract

Abstract A regioselective gold (I)‐catalyzed approach for the construction of polycyclic chromene cores has been developed. The reaction proceeds in good to excellent yields under mild condition with a broad range of substrates providing a simple and efficient tool for the synthesis of pyranochromene derivatives. Moreover, the regiochemical control of the annulation of unsymmetrically substituted propargylic ethers has been investigated focusing on electronic/steric effects of the ligands of gold complexes as well as on the electronic effects of the groups on the aromatic rings.

Topics & Concepts

ChemistryRegioselectivitySteric effectsIntramolecular forceAnnulationCatalysisCombinatorial chemistryElectronic effectOrganic chemistryComputational chemistryCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsSynthesis of Indole Derivatives
Synthesis of Polycyclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA) | Litcius