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1 article(s) from Finkbeiner, Peter

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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Graphical Abstract

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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Review

Published 30 May 2018

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