An organometallic approach to the synthesis of heteropolycyclic compounds from benzenes

Paolo Siano, Louis A. Diment, Daniel J. Siela, Megan N. Ericson, Matt McGraw, Benjamin F. Livaudais, Diane A. Dickie and W. Dean Harman ()
Additional contact information
Paolo Siano: University of Virginia
Louis A. Diment: University of Virginia
Daniel J. Siela: University of Virginia
Megan N. Ericson: University of Virginia
Matt McGraw: University of Virginia
Benjamin F. Livaudais: University of Virginia
Diane A. Dickie: University of Virginia
W. Dean Harman: University of Virginia

Nature Communications, 2025, vol. 16, issue 1, 1-9

Abstract: Abstract The emerging field of dearomatization capitalizes on the synthetic potential of aromatic molecules. By using a transition metal to bind to two carbons of a benzene ring, the remaining four carbons are left available for the attachment of various chemical fragments. If these fragments are connected, this process could be a blueprint for synthesizing polycyclic architectures. The objective of this study is to develop a modular approach for creating classes of saturated polycyclic compounds that are currently underrepresented in the landscape of druggable chemical space. Herein, the phenyl group of methylphenylsulfone is coordinated to the tungsten complex {WTp(NO)(PMe3)}, largely interrupting its aromatic stabilization because of strong metal-to-ligand backbonding. Through the combination of ester enolate and amine addition reactions to the arene carbons, a wide array of chemically diverse polyheterocyclic systems is prepared. The tungsten stereogenic center influences the configurations of 3-5 stereocenters derived from the phenyl carbons.

Date: 2025
References: Add references at CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-025-62835-2 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-62835-2

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-025-62835-2

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().