Copper‐Catalyzed Cyclization of Aryl Amines and Aryldiazonium Salts under Air: Access to <i>N</i>‐2‐Aryl‐Naphthotriazoles

Zhu, Chuanle; Zeng, Hao; Chen, Fulin; Liu, Chi; Jiang, Huanfeng

doi:10.1002/adsc.201900981

Cited by 16 publications

(7 citation statements)

References 57 publications

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“…In 2019, the same group continued to report a novel protocol for the synthesis of N 2 ‐aryl‐naphthotriazoles via copper‐catalyzed intermolecular cyclization of aryl amines and aryldiazonium salts (Scheme 22). [35] A variety of N 2 ‐aryl‐naphthotriazoles were produced from naphthalen‐2‐amines and aryldiazonium tetrafluoroborates in good to excellent yields, even on a gram scale. In addition, the control experiments revealed that a radical pathway might not be involved in this transformation.…”

Section: Synthesis Of 123‐triazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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Nitrogen heterocycles are important structural subunits that occur widely in bioactive natural products, pharmaceuticals, agrochemicals, dyes, cosmetics, and functional materials. Considering the importance of these useful compounds in modern science, the synthesis of N-heterocycles and their derivatives has always been a hot topic in organic synthesis. Recently, arenediazonium salts which can be easily prepared from inexpensive and abundantly available anilines, have been used as versatile nitrogen sources in the field of nitrogen heterocycle synthetic chemistry due to their ready availability, rich reactivity, and diverse transformations. The aim of the present review is to summarize the recent advances in the synthesis of nitrogen heterocycles using arenediazonium salts as nitrogen sources in the past ten years. Hopefully, it can provide practical guidance for the readers who are interested in utilizing arenediazonium salts as building blocks in organic synthesis. For simplicity and clarity, the organization of this review is based on the number of N atoms in the ring of nitrogen heterocycle.

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Section: Synthesis Of 123‐triazoles and Their Derivativesmentioning

confidence: 99%

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

et al. 2020

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“…1,2,3‐triazoles have widely spread in medicines with pharmaceutical and biological activities. Aryldiazonium salts, as nitrogen‐based synthons have been shown to undergo the annulation or cascade reactions with vinyl azides, [75] oxime acetates, [76] aryl amines, [77] ketene N,S‐acetals, [78] and alkyl 3‐aminoacrylates [79] to give planar tri‐substituted N2‐aryl‐1,2,3‐triazoles. In this context, Cu‐catalyzed annulation reaction of 2H ‐azirines and aryldiazonium salts had been studied by Ma and co‐workers to obtain a series of fully substituted N2‐aryl‐1,2,3‐triazoles as the final products in 42–96 % yields (Scheme 49).…”

Section: Reaction Of 2h‐azirinesmentioning

confidence: 99%

2H‐Azirines: Recent Progress in Synthesis and Applications

Xu,

Zeng,

Luo

et al. 2024

Eur J Org Chem

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2H‐arizines are important three‐membered heterocycles in organic chemistry. Recently, many advances in the synthesis and functionalization of 2H‐arizines have been reported. Neber rearrangement, isomerization of isoxazole, oxidation of enamine, C–H bond activation, decomposition of vinyl azide, functionalization of alkyne, and multi‐step synthesis have been developed for the efficient assembly of 2H‐azirines. As versatile and highly strained three‐membered unsaturated heterocycles, 2H‐azirines can be used as distinctive building blocks towards significant functional groups, and have attracted extensive attention for the fabrication of numerous heterocycles. Recent studies have focused on [3+n] ring‐expansion reactions, nucleophilic addition of C=N double bond or continuous nucleophilic addition followed by cyclization, ring‐opening of 2H‐azirines to acyclic compounds, and substitution of sp3‐C‐H of 2H‐azirines. One of the most critical challenges is seeking for a selective opening of the specific three bonds of the strained azirine circle, some of what can be achieved on the basis of metal catalyst, photocatalysis, or combination of metal catalyst and photocatalysis. In this review, recent advances involving the synthesis and reactivity of 2H‐arizines accompanied with challenges and breakthroughs are summarized. The review mainly covers the period from 2019 to 2023.

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“…The copper-catalyzed annulation cascade reactions of aryl diazonium salts with oxime acetates and arylamines were developed, affording N -2-aryl-1,2,3-triazoles and N -2-aryl-naphthotriazoles, respectively (Scheme ). In the previous case, the proposed mechanism involves a nucleophilic attack of copper(II) enamide complex at the terminal N atom of aryl diazonium salts, followed by the isomerization to obtain cyclic hydrazonyl iminyl copper(II) as the key intermediate 370 .…”

Section: Reactions With the Retention Of The Nitrogen Groupmentioning

confidence: 99%

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

et al. 2021

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Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance of aryl diazonium salts spanning most disciplines of the chemical sciences, we review the recent development of aryl diazonium chemistry over the past seven years (2013−2020). Special emphasis is put on various new transformations involving the generation of radical intermediates via thermal, photochemical, and electrochemical means. Recent advances in the development of transition metal-catalyzed reactions using aryl diazonium salts are also reviewed. Together, these newly developed transformations significantly expand the synthetic chemist's repertoire of aromatic carbon−carbon and carbon−heteroatom bond forming methods using aryl diazonium precursors, providing powerful tools for the synthesis and modification of complex molecular scaffolds.

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Copper‐Catalyzed Cyclization of Aryl Amines and Aryldiazonium Salts under Air: Access to N‐2‐Aryl‐Naphthotriazoles

Cited by 16 publications

References 57 publications

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

Recent Advances in the Synthesis of Nitrogen Heterocycles Using Arenediazonium Salts as Nitrogen Sources

2H‐Azirines: Recent Progress in Synthesis and Applications

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

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