Metal- and acid-free, TBN-mediated direct C H nitration of arenes

Xu, Guiying; Zhou, Li; Lv, Chengdong; Xian, Ming; Wang, Qinggang

doi:10.1016/j.jscs.2019.01.002

Journal of Saudi Chemical Society

2019

DOI: 10.1016/j.jscs.2019.01.002

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Metal- and acid-free, TBN-mediated direct C H nitration of arenes

Guiying Xu

Li Zhou

Chengdong Lv

et al.

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Cited by 4 publications

(1 citation statement)

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“…To the same vessel, 2a was added to perform the present cyanation, which provided 7 in 61% yield. In another example, a sequential aromatic C−H cyanation 19,20 of 8 and the present denitrative cyanation of the resulting 9 was performed, which successfully generated 10 in a moderate yield (Scheme 2B). A plausible mechanism for this reaction is as follows (Scheme 3).…”

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confidence: 99%

Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides

Iizumi,

Tanaka,

Muto

et al. 2024

Org. Lett.

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confidence: 99%

Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides

Iizumi,

Tanaka,

Muto

et al. 2024

Org. Lett.

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Catalyst‐Free Site‐Selective Diverse Functionalization of Inherent C–H Bonds in 1‐Aryl‐β‐carbolines, Norharmane and Harmine

et al. 2022

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A catalyst-free, site-selective diverse functionalization of latent CÀ H bonds in 1-aryl-β-carbolines and natural norharmane and harmine has been accomplished. This method enables the functionalization of 1-aryl-β-carbolines as C6-chlorination, C6bromination, and C4-nitration employing cost-effective, ecofriendly reagents such as trichloroisocyanuric acid (TCCA), Nbromosuccinimide (NBS) and tert-butyl nitrite (TBN), respectively. Pleasingly, these catalyst-/additive-free strategies were suitable with a broad range of substrate functionalities of different electronic nature, providing moderate to good yields of functionalized 1-aryl-β-carbolines. The critical/sensitive func-tionalities such as -CF 3 , -NO 2 , -CN, and 1-(thiophen-2-yl)-βcarboline were successfully employed, offering corresponding C6-halogenated or C4-nitrated products without strain. Furthermore, site-selective chlorination and bromination of two natural alkaloids such as harmine, norharmane were realized, resulting in corresponding halogenated products, including natural product eudistomin-N. In addition, we also employed these products in further diversification through -NO 2 reduction and Suzuki (CÀ C) coupling of brominated compounds to deliver a C6-arylated product.

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Solvent-controlled chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines with tert-butyl nitrite

Xuan-hua

Mahmood

et al. 2019

Org. Chem. Front.

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Metal- and acid-free, TBN-mediated direct C H nitration of arenes

Cited by 4 publications

References 66 publications

Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides

Palladium-Catalyzed Denitrative Synthesis of Aryl Nitriles from Nitroarenes and Organocyanides

Catalyst‐Free Site‐Selective Diverse Functionalization of Inherent C–H Bonds in 1‐Aryl‐β‐carbolines, Norharmane and Harmine

Solvent-controlled chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines with tert-butyl nitrite

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