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1 article(s) from Novák, Tamás T.

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

Attila Márió Remete,
Tamás T. Novák,
Melinda Nonn,
Matti Haukka,
Ferenc Fülöp and
Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

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Graphical Abstract

Scheme 1: Proposed outcome of the halofluorination of (rac)-1. Only the main conformers of (rac)-1 and (rac)-...

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Scheme 2: Halofluorination reactions of the trans-diester (rac)-1.

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Scheme 3: Probable outcomes of the halofluorination of 4. Both conformers of the compounds 4, (rac)-T2a,b, an...

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Scheme 4: Halofluorination reactions of the cis-diester 4. Important NOESY interactions are indicated by two-...

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Scheme 5: Halofluorination reactions of the cis-tetrahydrophthalic imide derivative 7.

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Scheme 6: Synthesis and halofluorination of the trans-imide (rac)-10.

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Figure 1: Crystal structure of (rac)-11b.

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Scheme 7: Synthesis of the cyclic carbamide (rac)-13.

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Scheme 8: Halofluorination reactions of the γ-lactam (rac)-14. Relevant NOESY interactions are indicated by t...

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Figure 2: Crystal structure of the product (rac)-15a.

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Figure 3: Crystal structure of the product (rac)-15b.

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Scheme 9: Reactions of the diester 16 with NBS or NIS in the presence or absence of Deoxo-Fluor^®.

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Scheme 10: Formation of the halolactons (rac)-17a,b. The initial attack of the halogen cation occurs at the st...

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Scheme 11: Unsuccessful halofluorination of the bicyclic diester 18.

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Scheme 12: Halofluorination reactions of the rigid tricyclic imine 19. The relevant NOESY interactions are mar...

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Scheme 13: Mechanism of the halofluorination reactions of the substrate 19. X = Br (compounds a), I (compounds...

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Scheme 14: Synthesis and halofluorination of the imide 24.

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Scheme 15: Cyclizations of halofluorinated diesters with potassium tert-butoxide. Relevant NOESY interactions ...

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Scheme 16: Mechanism of the reaction of the cyclopropanation of the compounds (rac)-2a,b and (rac)-5a with t-B...

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Scheme 17: Presumed mechanism of the reaction of the compound (rac)-6b with t-BuOK.

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Scheme 18: Cyclizations of halofluorinated tetrahydrophthalimides with DBU. Relevant NOESY interactions are ma...

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Scheme 19: Mechanism for the formation of (rac)-28 from (rac)-11a,b. Although the formation of the compound (r...

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Scheme 20: Fluoroselenations of the cyclohexenedicarboxylates (rac)-1 and 4.

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Scheme 21: PhSe⁺-induced lactonization of the diester 16. Relevant NOESY interactions are marked with two-head...

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Scheme 22: Oxidation of the fluoroselenide (rac)-30 under acidic and basic conditions.

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Scheme 23: Oxidation of the fluoroselenide mixture (rac)-31 under acidic and basic conditions.

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Published 16 Oct 2020

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