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• W3139007310 abstract "Abstract Saturated, fluorinated carbocycles are emerging as important modules for contemporary drug discovery. To expand the current portfolio, the synthesis of novel trifluorinated tetralins has been achieved. Fluorinated methyleneindanes serve as convenient precursors and undergo efficient difluorinative ring expansion with in situ generated p ‐TolIF 2 (>20 examples, up to >95 %). A range of diverse substituents are tolerated under standard catalysis conditions and this is interrogated by Hammett analysis. X‐ray analysis indicates a preference for the CH−F bond to occupy a pseudo ‐axial orientation, consistent with stabilising σ C−H →σ C−F * interactions. The replacement of the symmetric [CH 2 −CH 2 ] motif by [CF 2 −CHF] removes the conformational degeneracy intrinsic to the parent tetralin scaffold leading to a predictable half‐chair. The conformational behavior of this novel structural balance has been investigated by computational analysis and is consistent with stereoelectronic theory." @default.
• W3139007310 created "2021-03-29" @default.
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• W3139007310 date "2021-05-01" @default.
• W3139007310 modified "2023-10-10" @default.
• W3139007310 title "Trifluorinated Tetralins via I(I)/I(III)‐Catalysed Ring Expansion: Programming Conformation by [CH₂CH₂] → [CF₂CHF] Isosterism" @default.
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• W3139007310 doi "https://doi.org/10.1002/anie.202102222" @default.
• W3139007310 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/8251640" @default.
• W3139007310 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/33721384" @default.
• W3139007310 hasPublicationYear "2021" @default.
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