Formation of Heteropolycyclic Frameworks via the Dearomatization of a Dihapto-Coordinated Anisole
Year: 2025
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Heteropolycyclic frameworks are widely represented in biologically and pharmaceutically relevant compounds; however, methods to synthesize these frameworks often result in heterocycles containing predominantly sp 2 -hybridized carbons. Herein we describe a heteroannulation scheme featuring a double protonation of a tungsten η 2 -anisole complex. The resulting dicationic intermediate reacts with activated arenes through an electrophilic aromatic substitution reaction to form an oxocarbenium complex, which can be reduced to an allylic ether complex. Subsequent acidolysis results in a π-allyl complex that can react with alcohol or amine substituents of the activated arene reagent to form the desired heteropolycyclic core.
Source: Organometallics
Institution: University of Virginia
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G1842872291, G2430302282, Rapid Synthesis of Topologically Complex Molecules with Tungsten Dearomatization Agents, G5306823598, G7238273710, MRI: Acquisition of a rapid-throughput NMR spectrometer at the University of Virginia, MRI: Acquisition of a Single Crystal X-ray Diffractometer at the University of Virginia, Rapid Synthesis of Topologically Complex Molecules with Tungsten Dearomatization Agents
OpenAlex ID: W4416420838