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Media type:
E-Article
Title:
Strain‐Release Pentafluorosulfanylation and Tetrafluoro(aryl)sulfanylation of [1.1.1]Propellane: Reactivity and Structural Insight**
Contributor:
Kraemer, Yannick;
Ghiazza, Clément;
Ragan, Abbey N.;
Ni, Shengyang;
Lutz, Sigrid;
Neumann, Elizabeth K.;
Fettinger, James C.;
Nöthling, Nils;
Goddard, Richard;
Cornella, Josep;
Pitts, Cody Ross
Published:
Wiley, 2022
Published in:
Angewandte Chemie International Edition, 61 (2022) 48
Language:
English
DOI:
10.1002/anie.202211892
ISSN:
1521-3773;
1433-7851
Origination:
Footnote:
Description:
AbstractWe leveraged the recent increase in synthetic accessibility of SF5Cl and Ar−SF4Cl compounds to combine chemistry of the SF5and SF4Ar groups with strain‐release functionalization. By effectively adding SF5and 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⋅⋅⋅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.