A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

Chatterjee, Nachiketa; Bhatt, Divya; Goswami, Avijit

doi:10.1039/c5ob00337g

Cited by 26 publications

(16 citation statements)

References 27 publications

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“…In a related work, Goswami and co‐workers developed a transition‐metal‐free oxidative ipso ‐nitration of organoboronic acids 78 at room temperature using a combination of hypervalent iodine source [bis(trifluoroacetoxy)]iodobenzene (PIFA), N ‐bromosuccinimide (NBS) and NaNO 2 (Scheme ) . The protocol was shown to work over a broad range of substrates including aryl, heteroaryl moiety, alkylboronic acids to efficiently yield the corresponding nitro derivatives.…”

Section: Nano2 As Nitrating Agentmentioning

confidence: 99%

Applications of Sodium Nitrite in Organic Synthesis

Mukhopadhyay

Batra

2019

Eur J Org Chem

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Sodium nitrite (NaNO2) is a cheap inorganic reagent that has wide applications in synthetic organic chemistry. The Sandmeyer reaction for transforming amines into diazo derivatives and nitration, including the oxidative ones, are well known and globally used in several industrial processes too. Sodium nitrite is also used in the Nef reaction and Abidi transformation besides several other important reactions. The ability of NaNO2 to produce NO·, NO2, and N2O4 under oxidative conditions has considerably assisted in the discovery of its newer applications. Strikingly, this has resulted in remarkable development in reactions involving NaNO2 as either catalyst or reagent, and this review is an attempt to assimilate them. Wherever possible the mechanistic details associated with the reported reaction/transformation is provided.

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Section: Nano2 As Nitrating Agentmentioning

confidence: 99%

Applications of Sodium Nitrite in Organic Synthesis

Mukhopadhyay

Batra

2019

Eur J Org Chem

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“…In this context, developing a more selective and milder method for nitration continues to be an important issue in the field of organic chemistry. In the last few decades, a significant breakthrough in nitration protocols, namely, the ipso ‐nitration of aryl boronic acids was reported by Prakash and Olah,– and several improved nitrating protocols– have also appeared. In addition, nitration via metal‐catalyzed transformation was developed.…”

Section: Figurementioning

confidence: 99%

Ipso Nitration of 2‐Halothiophenes with Silver Nitrate

et al. 2017

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As imple methodf or the ipso nitration of aryl substituted2 -halothiophenes that produces 2-nitrothiophenes with regioselectivityi sd escribed. The method involves AgNO 3 as the nitration reagent withoutf urther additives to conductt he transformation. 2-Styryl-5-halothiophenes and the bisthienyl derivatives could be smoothly converted to the corresponding ipso-nitration productsi n good yields. This transformation is believed to proceed via an Ag III intermediate and oxygen absorption.Nitration is one of the most fundamental and important transformationsi no rganic synthesis for introducing an itro group into an aromatic compound, which can then be easily converted to the corresponding nitrogen functional groups or used in furthert ransformations. [1] Aromatic nitro compounds have functioned as key synthons in av ariety of reactions, including the preparation of dyes, pharmaceuticals andm aterials cience. [1, 2] In aromatic compounds, the most common method involves reacting the aromatic compound with HNO 3 and a strong acid or dinitrogen pentoxide via electrophilica romatic substitutions. [1] Although an umber of alternative routes have been published in the past few decades, these electrophilic methods usuallyr esult in isomeric mixtureso fn itrated products. [1c] In addition, the use of strong acids and oxidants restricts the scope of such reactions. In this context, developing am ore selective and milder method for nitration continues to be an important issue in the field of organicc hemistry.I nt he last few decades, as ignificant breakthrough in nitration protocols, namely,the ipso-nitration of aryl boronic acids was reported by Prakash and Olah, [3a-c] and several improved nitrating protocols [3d-g] have also appeared. In addition, nitration via metal-catalyzed transformation was developed. Saito and Koizumi [4a] reportedo nt he copper-catalyzed nitration of iodoarene derivatives, and Buchwald and Fors [4b] reportedo nt he nitration of aryl chlorides, triflates,a nd nonaflates using ap alladium catalyst. Subsequent to that report, severala lternate metal-catalyzed nitration systems werea lso reported. [4c-h] Asian

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“…Chatterjee et al reported a highly efficient [bis-(trifluoroacetoxy)]iodobenzene (PIFA)-mediated oxidative regioselective nitration of aryl-, alkyl-and heteroarylboronic acids, with their first example being the use of a PIFA-NBS-NaNO2 combination to generate nitroarenes under transition metal-free conditions. 39 In their study, it was observed that the presence as well as the amount of an additive (NBS) is important for better conversion of the organoboronic acids to the nitroarenes. Increasing the amount of NBS to 2.1 eq.…”

Section: ------------------------------------------------------------mentioning

confidence: 99%

Recent advances in ipso-nitration reactions

Bozorov¹,

Zhao²,

Aisa³

et al. 2016

Arkivoc

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In the present review the various types of ipso-nitration reactions, in particular those advances in ipsonitration reactions that have been reported since the beginning of this century (i.e., from [2000][2001][2002][2003][2004][2005][2006][2007][2008][2009][2010][2011][2012][2013][2014][2015] are discussed. The review highlights the recent developments of the ipso-nitration reactions, a variety of the differences between traditional and modern methods for performing ipso-nitration reactions, as well as the most novel approaches to performing these reactions. In addition, the proposed mechanisms of ipso-nitration reactions are discussed.

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A novel transition metal free [bis-(trifluoroacetoxy)iodo]benzene (PIFA) mediated oxidative ipso nitration of organoboronic acids

Cited by 26 publications

References 27 publications

Applications of Sodium Nitrite in Organic Synthesis

Applications of Sodium Nitrite in Organic Synthesis

Ipso Nitration of 2‐Halothiophenes with Silver Nitrate

Recent advances in ipso-nitration reactions

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