4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 143, Issue 34, Pages 13501-13506

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.1c07187

Keywords

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Funding

  1. National Science Foundation [CHE-1665389, NSF/MRI 1229400]
  2. NIH Shared Instrumentation Grant program [S10OD011952]
  3. National Institutes of Health Cancer Center Support Grant [CA-77598]

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This study presents a sulfurane-mediated method for the formation of dimeric dibenzofuran helicenes under thermal conditions. Experimental and DFT studies support a ligand coupling mechanism involving tetracarbo-ligated S(IV) intermediates, resulting in the generation of polycyclic aromatic compounds with the de novo generation of five new rings in a single operation.
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.

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