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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Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Organic Letters, Journal Year: 2024, Volume and Issue: 26(15), P. 3091 - 3096

Published: April 3, 2024

Presented herein is a novel synthesis of pharmaceutically privileged spiroindoline derivatives via cascade reactions N-methyl-N-nitrosoanilines with diazo homophthalimides. A group mechanistic studies disclosed that the formation product involves an unusual reaction mode N-methyl-N-nitrosoaniline featuring initial C(sp2)–H bond activation/alkylation followed by C(sp3)–H activation/spiroannulation. To our knowledge, this first example in which acts as C3N1 synthon to accomplish formal [4+1] spiroannulation participation N-methyl unit rather than previously reported C2N1 undergo [3+2] annulation without unit. In general, newly developed synthetic protocol features simple and readily accessible starting materials, valuable products, unique mechanism, high efficiency atom-economy, excellent compatibility diverse functional groups, ready scalability.

Language: Английский

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Synthesis of functionalized quinolines from the cascade reactions of N-aryl amidines with two CF₃-ynones via C–H/N–H/C–N/C–C bond cleavage

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1917 - 1923

Published: Jan. 1, 2024

We present a novel synthesis of CF 3 - and alkynyl-substituted quinoline derivatives based on Rh( iii )-catalyzed cascade reactions N -aryl amidines with two -ynones. Then, some products are transformed into polycyclic -benzo[ k ]phenanthridines through an intramolecular annulation reaction.

Language: Английский

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Synthesis of Indenone-Fused Pyran Derivatives from Aryl Enaminones and Cyclopropenones through Unsymmetrical Relay C–H Bond Activation and Double C–C/C–O Bond Formation

Organic Letters, Journal Year: 2024, Volume and Issue: 26(31), P. 6602 - 6607

Published: July 30, 2024

Presented herein is a novel synthesis of indenone-fused pyran derivatives via the cascade reactions aryl enaminones with cyclopropenones. The formation products involves one-pot procedure consisting C–H bond and enamine functionalization along C–C cleavage cyclopropenone 1,3-rearrangement in situ-formed allylic alcohol moiety followed by intramolecular O-nucleophilic addition Me2NH elimination. To our knowledge, this first simultaneous both indenone scaffolds through concurrent unsymmetrical relay activation double C–C/C–O formation. Moreover, usefulness method further showcased its suitability for large-scale synthetic scenarios diverse transformations products.

Language: Английский

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Synthesis of CF₃–Isoquinolinones and Imidazole-Fused CF₃–Isoquinolinones Based on C–H Activation-Initiated Cascade Reactions of 2-Aryloxazolines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10180 - 10196

Published: July 4, 2024

Presented herein are novel syntheses of CF

Language: Английский

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Synthesis of Naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-Catalyzed C6/C5 Dual C–H Functionalization of N-Pyridyl-2-pyridones with Diazonaphthalen-2(1H)-ones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(4), P. 786 - 791

Published: Jan. 22, 2024

Presented herein is an unprecedented synthesis of naphtho[1′,2′:4,5]furo[3,2-b]pyridinones via Ir(III)-catalyzed C6/C5 dual C–H functionalization N-pyridyl-2-pyridones with diazonaphthalen-2(1H)-ones. This protocol forms C–C and C–O bonds in one pot which diazonaphthalen-2(1H)-ones serve as bifunctional reagents, providing both alkyl aryloxy sources. To the best our knowledge, this first example title compounds by using substrates. Notably, method features operational simplicity, good functional group tolerance, high efficiency, atom economy.

Language: Английский

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Condition‐Controlled Selective Synthesis of CF₃‐Chromene and CF₃‐Benzofuran from N‐Phenoxyacetamide and CF₃‐Ynone

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: March 27, 2025

Comprehensive Summary Presented herein is a condition‐controlled selective synthesis of CF 3 ‐chromene and ‐benzofuran based on the reaction N ‐phenoxyacetamide ‐ynone. When carried out in MeOH under catalysis Rh(III), formed via C—H metalation‐initiated alkenylation, acetamide group migration intramolecular oxo ‐nucleophilic addition. On other hand, when run DMSO promotion CsOAc, generated aza ‐Michael addition‐initiated [3,3]‐σ rearrangement, addition water elimination. To our knowledge, this first report construction chromene or benzofuran scaffold along with introduction unit from same starting materials. The methodology was scalable products could be readily transformed into valuable products. Moreover, thus obtained possess decent anticancer activity.

Language: Английский

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Application of Sulfoxonium Ylides or Iodonium Ylides in Rhodium‐Catalyzed Synthesis of Phenanthrenes

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(8), P. 1744 - 1750

Published: Feb. 22, 2024

Abstract The transmetalation triggered rhodium‐catalyzed C−H bond activation and tandem annulation of 2‐biphenylboronic acids with sulfoxonium ylides or iodonium has been developed. Various products phenanthrenes were constructed under redox‐neutral conditions in 34–86% yields. Several mechanism exploration experiments derivatization reactions conducted sequence to gain a deeper understanding the process potential this transformation. It offers an alternative approach for synthesis phenanthrene derivatives.

Language: Английский

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Synthesis of CF₃-Substituted N-Heterocyclic Compounds Based on C–H Activation-Initiated Formal [2 + 3] Annulation Featuring with a Latent Nucleophilic Site

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(11), P. 7828 - 7842

Published: May 22, 2024

Presented herein is a novel synthesis of CF

Language: Английский

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Divergent synthesis of pyrrolizine derivatives through C−H bond functionalization of pyrroles

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(51), P. 6536 - 6539

Published: Jan. 1, 2024

Presented herein is the synthesis of diversely functionalized pyrrolizines from reaction

Language: Английский

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