Rapid Microwave-Assisted Copper-Catalyzed Nitration of Aromatic Halides with Nitrite Salts

Paik, Seung Uk; Jung, Myoung Geun

doi:10.5012/bkcs.2012.33.2.689

Cited by 12 publications

(8 citation statements)

References 16 publications

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“…Most studies on the synthesis of aromatic nitro compounds have focused on electrophilic nitration of arenes, leading to low region selectivity and overnitration . To resolve this issue, ipso -nitration of aryl bromides and iodides was performed to produce these compounds via copper-catalyzed Ullmann-type couplings (Scheme A) . In recent years, the ipso -nitration of aryl chlorides has been achieved under palladium-catalyzed conditions by Buchwald and Fors (Scheme A) .…”

Section: Introductionmentioning

confidence: 99%

“…In the aforementioned copper- or palladium-catalyzed ipso -nitration of aryl halides, the mechanisms were proposed via an oxidative addition/reductive elimination process (two-electron transfer). , Indeed, iron complexes can engage in two-electron transfer procedures . However, single-electron transfer (SET) is competitive and preferred in some situations .…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

et al. 2021

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A photoinduced iron-catalyzed ipso-nitration of aryl halides with KNO 2 has been developed, in which aryl iodides, bromides, and some of aryl chlorides are feasible. The mechanism investigations show that the in situ formed iron complex by FeSO 4 , KNO 2 , and 1,10-phenanthroline acts as the light-harvesting photocatalyst with a longer lifetime of the excited state, and the reaction undergoes a photoinduced single-electron transfer (SET) process. This work represents an example for the photoinduced iron-catalyzed Ullmann-type couplings.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

et al. 2021

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“…11 Several reports describe how to substitute bromine by nitro groups via copper-catalysed reactions involving nitrite salts. [31][32][33] However, such reaction led to the decomposition of 1,7-Br2PTE. Interestingly, the replacement of a bromine atom by a nitro group was reported on thiophene derivatives by the simple use of silver nitrate.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 1,6/7-(NO2)2Perylenediimide and 1,6/7-(NH2)2Perylenediimide: Regioisomerically Pure Materials for Organic Electronics

Gapin

David

Allain

et al. 2023

Preprint

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The use of perylenediimide (PDI) building blocks in materials for organic electronic is of considerable interest. The introduction of peripheral groups in their ortho and bay positions radically modify their optoelectronic properties. In this article, we describe an efficient method to afford regioisomerically pure 1,6/7-(NO2)2- and (NH2)2-PDIs employing two key steps: the selective crystallization of 1,6-(NO2)2-perylene-3,4,9,10-tetracarboxy tetrabutylester and the nitration of regiopure 1,7-Br2-PDI with silver nitrite. The optoelectronic properties of the resulting regioisomerically pure dinitro, diamino-PDIs and bisazacoronenediimides (BACDs) are reported and demonstrate the need to separate both regioisomers of such n-type organic semiconductors for their inclusion in advanced optoelectronic devices.

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“…The reaction proceed smoothly using copper(II) chloride (CuCl 2 ) as catalyst, KOH as base and tetrabutylammonium bromide [(n-Bu) 4 NBr] as phase transfer catalyst and L-proline lithium salt as ligand, the resulting mixture was then heated in a microwave at 120 • C for 40 min to produce phenol derivatives in moderate to excellent yield, Scheme 77. Aryl halides were converted into the corresponding nitro derivatives via coppercatalyzed microwave-assisted nitration using nitrite salts (n-Bu 4 NNO 2 ) [138]. A systematic optimization of the reaction has resulted in the use of catalytic amount (10 mol %) of CuI, N,N'-dimethylethylenediamine as ligand, and n-Bu 4 NNO 2 as nitrite salt, the reaction mixture was then heated in a microwave oven at 120 • C for 10 min to produce nitrobenzene derivatives in low to excellent yield, Scheme 78.…”

Section: Miscellaneous Synthesismentioning

confidence: 99%

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

Baqi

2020

Catalysts

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Cross-coupling reactions furnishing carbon–carbon (C–C) and carbon–heteroatom (C–X) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Ullmann, Ullman–Goldberg, Cadiot–Chodkiewicz, Castro–Stephens, and Corey–House, utilizing elemental copper or its salts as catalyst have, for decades, attracted and inspired scientists. However, these reactions were suffering from the range of functional groups tolerated as well as severely restricted by the harsh reaction conditions often required high temperatures (150–200 °C) for extended reaction time. Enormous efforts have been paid to develop and achieve more sustainable reaction conditions by applying the microwave irradiation. The use of controlled microwave heating dramatically reduces the time required and therefore resulting in increase in the yield as well as the efficiency of the reaction. This review is mainly focuses on the recent advances and applications of copper catalyzed cross-coupling generation of carbon–carbon and carbon–heteroatom bond under microwave technology.

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Rapid Microwave-Assisted Copper-Catalyzed Nitration of Aromatic Halides with Nitrite Salts

Cited by 12 publications

References 16 publications

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

Photoinduced Iron-Catalyzed ipso-Nitration of Aryl Halides via Single-Electron Transfer

Synthesis of 1,6/7-(NO2)2Perylenediimide and 1,6/7-(NH2)2Perylenediimide: Regioisomerically Pure Materials for Organic Electronics

Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions

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