Recent Progress in Synthetic Applications of Hypervalent Iodine(III) Reagents

Chemical Reviews, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 13, 2024

Hypervalent iodine(III) compounds have found wide application in modern organic chemistry as environmentally friendly reagents and catalysts. iodine are commonly used synthetically important halogenations, oxidations, aminations, heterocyclizations, various oxidative functionalizations of substrates. Iodonium salts arylating reagents, while iodonium ylides imides excellent carbene nitrene precursors. Various derivatives benziodoxoles, such azidobenziodoxoles, trifluoromethylbenziodoxoles, alkynylbenziodoxoles, alkenylbenziodoxoles group transfer the presence transition metal catalysts, under metal-free conditions, or using photocatalysts photoirradiation conditions. Development hypervalent catalytic systems discovery highly enantioselective reactions chiral represent a particularly recent achievement field chemistry. Chemical transformations promoted by many cases unique cannot be performed any other common, non-iodine-based reagent. This review covers literature published mainly last 7-8 years, between 2016 2024.

Language: Английский

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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7214 - 7219

Published: Sept. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Language: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 36(1), P. 109799 - 109799

Published: March 20, 2024

Language: Английский

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Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5660 - 5666

Published: Jan. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Language: Английский

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Catalytic C H activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109494 - 109494

Published: Jan. 6, 2024

Language: Английский

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Metal-free synthesis of difluoro/trifluoromethyl carbinol-containing chromones via tandem cyclization of o-hydroxyaryl enaminones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(46), P. 9236 - 9241

Published: Jan. 1, 2023

A convenient and efficient method for the synthesis of difluoro/trifluoromethyl carbinol-containing chromone derivatives has been developed.

Language: Английский

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Co(III)-Catalyzed Coupling of Enaminones with Oxadiazolones for Imidazole Synthesis

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Aug. 30, 2024

Appendage speciation-oriented synthesis, as opposed to the conventional wisdom of skeleton is reported herein, emphasizing maximization type-, position-, and configuration-variance appendages. A Co(III) catalytic protocol in accordance with this synthetic modality has been established for coupling enaminones oxadiazolones imidazoles, allowing achievement full position-variance This translates an expanded reaction structural development scope can provide fertile ground productive organic synthesis.

Language: Английский

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Rh(iii)-catalyzed C(sp²)–H functionalization/[4+2] annulation of oxadiazolones with iodonium ylides to access diverse fused-isoquinolines and fused-pyridines

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6560 - 6563

Published: Jan. 1, 2024

A Rh( iii )-catalyzed C–H/N–H [4+2] annulation of oxadiazolones with iodonium ylides was developed, which afforded a series fused-isoquinolines and fused-pyridines.

Language: Английский

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Recent Advances in Site Selective Transformations of β-Enaminones via C-H Functionalization/Annulation

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

β-Enaminone transformation strategies are widely employed in the synthesis of numerous biologically active drugs and natural products, highlighting their significance medicinal chemistry.

Language: Английский

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