Hypervalent iodine(<scp>iii</scp>) promoted C–H/C–H amination/annulation tandem reactions: synthesis of benzimidazoles from simple anilines and aldehydes

Long, L. H.; Li, Xin; Tu, Mengshi; Zhang, Yekun; Qiao, Liang; Luo, Wei; Chen, Zhengwang

doi:10.1039/d2qo01644c

Cited by 6 publications

(1 citation statement)

References 75 publications

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“…The synthesis of benzimidazoles from anilines and aldehydes using acetoxybenziodoxoles as reagents was reported by Long and Chen's group. [172] In this reaction, aryl aldehydes 111 and anilines 112 react with acetoxybenziodoxole 100 upon heating in the presence of a zinc catalyst to form the corresponding products 113 (Scheme 41). This reaction also works for aromatic substrates 112 with alkynyl or alkenyl substituents and aliphatic aldehydes.…”

Section: Alkoxy- Nitrooxy- and Acyloxybenziodoxolesmentioning

confidence: 99%

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

2023

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Hypervalent iodine compounds have found broad application in modern organic chemistry as reagents and catalysts. Cyclic hypervalent iodine reagents based on the benziodoxole heterocyclic system have higher stability compared to their acyclic analogues, which makes possible the preparation and safe handling of the reagents with special ligands such as azido, cyano, and trifluoromethyl groups. Numerous iodine‐substituted benziodoxole derivatives have been prepared and utilized as reagents for transfer of the substituent on hypervalent iodine to organic substrate. Reactions of these reagents with organic substrates can be performed under metal‐free conditions, in the presence of transition metal catalysts, or using photocatalysts under photoirradiation conditions. In this review, we focus on the most recent synthetic applications of cyclic hypervalent iodine(III) reagents with the following ligands: N3, NHR, CN, CF3, SCF3, OR, OAc, ONO2, and C(=N2)CO2R. The review covers literature published mainly in the last 5 years.magnified image

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Section: Alkoxy- Nitrooxy- and Acyloxybenziodoxolesmentioning

confidence: 99%

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

2023

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

Yoshimura,

Zhdankin

2024

Chem. Rev.

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

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Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis

Long

Wang

et al. 2023

J. Org. Chem.

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Herein, we disclose a practical and simple procedure to synthesize 2-aminobenzoxaoles. Simple anilines and formamides were used as substrates. The C−H bond ortho to the amino group in the anilines was directly functionalized under cobalt-catalyzed conditions with high levels of functional group tolerance. Hypervalent iodine(III) was both an oxidant and a Lewis acid for this reaction. The mechanism study showed that this transformation may involve a radical process.

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Hypervalent iodine(iii) promoted C–H/C–H amination/annulation tandem reactions: synthesis of benzimidazoles from simple anilines and aldehydes

Abstract: A novel zinc-catalyzed hypervalent iodine mediated cascade transformation of anilines and aldehydes to benzimidazoles was developed. A series of 1,2-disubstituted benzimidazoles were achieved with aromatic, heteroaromatic, and aliphatic aldehydes. In...

Cited by 6 publications

References 75 publications

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

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

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

Cobalt-Catalyzed Hypervalent Iodine(III) Promoted Cascade Annulation Reaction of Anilines with Formamides for 2-Aminobenzoxazoles Synthesis

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