Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 48, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202211892
Keywords
Main Group Chemistry; Pentafluorosulfanyl; Propellane; Strained Molecules; X-Ray Diffraction
Categories
Funding
- National Science Foundation [CHE-1531193]
- Max-Planck-Gesellschaft
- Fonds der Chemischen Industrie (FCI-VCI)
- Boehringer Ingelheim Foundation
- University of California, Davis
- Alexander von Humboldt Stiftung
- Max-Planck-Institut fur Kohlenforschung
- Projekt DEAL
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By leveraging the accessibility of SF5Cl and Ar-SF4Cl compounds, we combined the chemistry of SF5 and SF4Ar groups with strain-release functionalization to synthesize structurally unique bicyclopentanes bearing distinct bioisosterism elements. These previously unknown structures not only expand the options for highly desired three-dimensional fluorinated building blocks but also provide insights into a more general effect observed in bicyclopentanes.
We leveraged the recent increase in synthetic accessibility of SF5Cl and Ar-SF4Cl compounds to combine chemistry of the SF5 and SF4Ar groups with strain-release functionalization. By effectively adding SF5 and SF4Ar radicals across [1.1.1]propellane, we accessed structurally unique bicyclopentanes, bearing two distinct elements of bioisosterism. Upon evaluating these hybrid isostere motifs in the solid state, we measured exceptionally short transannular distances; in one case, the distance rivals the shortest nonbonding C center dot center dot center dot C contact reported to date. This prompted SC-XRD and DFT analyses that support the notion that a donor-acceptor interaction involving the wing C-C bonds is playing an important role in stabilization. Thus, these heretofore unknown structures expand the palette for highly coveted three-dimensional fluorinated building blocks and provide insight to a more general effect observed in bicyclopentanes.
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