Convenient, metal-free <i>ipso</i>-nitration of arylboronic acids using nitric acid and trifluoroacetic acid

Shen, Guodong; Zhao, Lu; Liu, Wanxing; Huang, Xianqiang; Song, Huina; Zhang, Tongxin

doi:10.1080/00397911.2016.1244690

Cited by 7 publications

(3 citation statements)

References 18 publications

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“…Regioselectivity, metal‐free condition & inexpensive reagents are notable advantages of this technique. However, mechanism of this reaction is not yet clear by authors [47] …”

Section: Nitration By Transition Metal‐free Catalystmentioning

confidence: 99%

“…However, mechanism of this reaction is not yet clear by authors. [47] An efficient protocol for nitration of phenol investigated by Srinivas and co-authors by using Prussian blue and sodium nitrite in aqueous bisulfate and acetonitrile medium (Scheme 39). Kinetic study revealed that the reaction was followed second order.…”

Section: Nitration By Transition Metal-free Catalystmentioning

confidence: 99%

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Synthetic Protocols for Aromatic Nitration: A Review

Patel

2021

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Nitration of aromatic compounds represents a powerful and widely used transformation that allows introducing nitro group into aromatic systems. New synthetic strategies for aromatic nitration are deeply needed, including highly efficient and selective nitration methods. Aromatic nitration plays an important part in the industry, as the main use of nitration is to produce important products such as dyes & intermediate compounds, drugs, and Agrochemicals. The electrophilic aromatic nitration is most studied and important transformation in industrial process. This review will describe different possible methodologies that apply to this fundamental transformation with special attention to the most recent development that lasted from 2017–2020. The main pros and cons of recent nitration methods are briefly described with their specific reaction mechanism and highlighting the most important feature of the present aromatic nitration method.

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“…Regioselectivity, metal‐free condition & inexpensive reagents are notable advantages of this technique. However, mechanism of this reaction is not yet clear by authors [47] …”

Section: Nitration By Transition Metal‐free Catalystmentioning

confidence: 99%

Section: Nitration By Transition Metal-free Catalystmentioning

confidence: 99%

Synthetic Protocols for Aromatic Nitration: A Review

Patel

2021

ChemistrySelect

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“… Mononitrated and dinitrated products were observed for most arylboronic acids. In the past few years, various nitro and nitroso sources have been utilized to improve this methodology by the groups of Prakash, Wu and Beller, Fu, Maiti, Goswami, Shen, and Zolfigol, among others (see Figure ). Of all the reported literature, most methods require the use of unstable reagents, harsh and oxidative conditions, and long reaction times, and they display poor functional group tolerance, in addition to the release of superstoichiometric amounts of acidic or metal waste.…”

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confidence: 99%

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- and Heteroarylboronic Acids

et al. 2020

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Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

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