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3 article(s) from Boelke, Andreas

Synthesis and reactivity of azole-based iodazinium salts

Thomas J. Kuczmera,
Annalena Dietz,
Andreas Boelke and
Boris J. Nachtsheim

Beilstein J. Org. Chem. 2023, 19, 317–324, doi:10.3762/bjoc.19.27

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Figure 1: Nitrogen-containing iodolium and iodonium salts.

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Figure 2: Synthesis of a set of azoiodazinium salts 5. Method A: Iodoarene 4 (200 µmol) and mCPBA (1.1 equiv)...

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Figure 3: Single crystal structures (ORTEP drawing with 50% probability) of the pyrazole-coordinated salt 5bb...

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Scheme 1: Derivatizations of the iodonium salt 5aa. a) Ac₂O, CuSO₄·5H₂O, NaOAc, AcOH, 120 °C, 5 h; b) S₈/Se/T...

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Scheme 2: Post-functionalization of mono- and dicationic iodonium salts under preservation of the hypervalent...

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Full Research Paper

Published 16 Mar 2023

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Thermal stability of N-heterocycle-stabilized iodanes – a systematic investigation

Andreas Boelke,
Yulia A. Vlasenko,
Mekhman S. Yusubov,
Boris J. Nachtsheim and
Pavel S. Postnikov

Beilstein J. Org. Chem. 2019, 15, 2311–2318, doi:10.3762/bjoc.15.223

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Figure 1: General structure of aryl-λ³-iodanes.

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Figure 2: T_peak and ΔH_dec-values for a range of N- and O-substituted iodanes.

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Figure 3: TGA/DSC curves of (a) benziodoxolone 1, (b) triazole 2 and (c) pyrazole 6.

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Figure 4: Decomposition enthalpy (ΔH_dec) scale for pseudocyclic tosylates 1–15 and cyclic iodoso species 16 a...

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Figure 5: Correlation between the relative reactivity for pseudocyclic NHIs based on the reaction time in the...

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Figure 6: T_peak and ΔH_dec values for a range of N- and O-substituted iodanes.

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Figure 7: Decomposition enthalpy (ΔH_dec) scale for (pseudo)cyclic mesitylen(phenyl)- λ³-iodanes 18–33.

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Figure 8: TGA/DSC curves for the benzimidazole based diaryliodonium salt 25.

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Figure 9: TGA/DSC curves for the cyclic triazole 32.

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Scheme 1: The thermal decomposition of (pseudo)cyclic N-heterocycle-stabilized mesityl(aryl)-λ³-iodanes 25 an...

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Published 27 Sep 2019

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Atom-economical group-transfer reactions with hypervalent iodine compounds

Andreas Boelke,
Peter Finkbeiner and
Boris J. Nachtsheim

Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108

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Scheme 1: Overview of different types of iodane-based group-transfer reactions and their atom economy based o...

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Scheme 2: (a) Structure of diaryliodonium salts 1. (b) Diarylation of a suitable substrate A with one equival...

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Scheme 3: Synthesis of biphenyls 3 and 3’ with symmetrical diaryliodonium salts 1.

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Scheme 4: Synthesis of diaryl thioethers 5.

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Scheme 5: Synthesis of two distinct S-aryl dithiocarbamates 7 and 7’ from one equivalent of diaryliodonium sa...

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Scheme 6: Synthesis of substituted isoindolin-1-ones 9 from 2-formylbenzonitrile 8 and the postulated reactio...

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Scheme 7: Domino C-/N-arylation of indoles 10.

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Scheme 8: Domino modification of N-heterocycles 12 via in situ-generated directing groups.

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Scheme 9: Synthesis of triarylamines 17 through a double arylation of anilines.

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Scheme 10: Selective conversion of novel aryl(imidazolyl)iodonium salts 1b to 1,5-disubstituted imidazoles 18.

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Scheme 11: Selected examples for the application of cyclic diaryliodonium salts 19.

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Scheme 12: Tandem oxidation–arylation sequence with (dicarboxyiodo)benzenes 20.

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Scheme 13: Oxidative α-arylation via the transfer of an intact 2-iodoaryl group.

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Scheme 14: Tandem ortho-iodination/O-arylation cascade with PIDA derivatives 20b.

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Scheme 15: Synthesis of meta-N,N-diarylaminophenols 28 and the postulated mechanism.

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Scheme 16: (Dicarboxyiodo)benzene-mediated metal-catalysed C–H amination and arylation.

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Scheme 17: Postulated mechanism for the amination–arylation sequence.

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Scheme 18: Auto-amination and cross-coupling of PIDA derivatives 20c.

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Scheme 19: Tandem C(sp³)–H olefination/C(sp²)–H arylation.

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Scheme 20: Atom efficient functionalisations with benziodoxolones 36.

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Scheme 21: Atom-efficient synthesis of furans 39 from benziodoxolones 36a and their further derivatisations.

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Scheme 22: Oxyalkynylation of diazo compounds 42.

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Scheme 23: Enantioselective oxyalkynylation of diazo compounds 42’.

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Scheme 24: Iron-catalysed oxyazidation of enamides 45.

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Published 30 May 2018

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