Sulfurane [S(IV)]-Mediated Fusion of Benzynes Leads to Helical Dibenzofurans

Casey B. Ritts, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

Here we disclose a sulfurane-mediated method for the formation of dimeric dibenzofuran helicenes via the reaction between diaryl sulfoxides and hexadehydro-Diels-Alder (HDDA) derived benzynes. A variety of S-shaped and U-shaped helicenes were formed under thermal conditions. Both experimental and DFT studies support a sulfur(IV)-based coupling (aka ligand coupling) mechanism involving tetracarbo-ligated S(IV) intermediates undergoing reductive elimination to afford the helicene products. This process involves the de novo generation of five new rings in a single operation and constitutes a new method for the construction of topologically interesting, polycyclic aromatic compounds.

Original languageEnglish (US)
Pages (from-to)13501-13506
Number of pages6
JournalJournal of the American Chemical Society
Volume143
Issue number34
DOIs
StatePublished - Sep 1 2021

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© 2021 American Chemical Society.

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