Regioselective CH Imidation of Five‐Membered Heterocyclic Compounds through a Metal Catalytic or Organocatalytic Approach

Wang, Xin; Sun, Kai; Lv, Yunhe; Ma, Fengji; Li, Gang; Li, Donghui; Zhu, Zhong‐Hong; Jiang, Yongqing; Zhao, Feng

doi:10.1002/asia.201403052

Cited by 30 publications

(6 citation statements)

References 76 publications

(48 reference statements)

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“…Conventionally, transition metal-catalyzed aminations of carbon–halogen bonds in halogenated arenes are largely regarded as reliable and versatile . As an emerging synthetic route, transition metal-catalyzed aryl C–H aminations − have become an alternative to conventional amination. However, this approach is still in its infancy and has several disadvantages such as (1) the necessity for a directing group, (2) the requirement for a large excess of arene, and (3) limited substrate scope especially for 5-membered heterocycles .…”

mentioning

confidence: 99%

Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics

2015

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Versatile imidation of aromatic C-H bonds was accomplished. In the presence of copper bromide and 6,6'-dimethyl-2,2'-bipyridyl, a range of aromatics, such as polycyclic aromatic hydrocarbons, aromatic bowls, porphyrins, heteroaromatics, and natural products, can be imidated by N-fluorobenzenesulfonimide. A dramatic ligand-accelerated copper catalysis and an interesting kinetic profile were uncovered.

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confidence: 99%

Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics

2015

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“…Sun and Zhao reported copper-catalyzed C–H/N–H-type imidation of furans, thiophenes, and pyrroles by using t BuOOH as an oxidant (Scheme .) . Li and Duan showed the same reaction with nickel catalyst .…”

Section: C–h Amination Of 5-membered Heteroarenesmentioning

confidence: 60%

“…Sun and Zhao reported copper-catalyzed C−H/N−H-type imidation of furans, thiophenes, and pyrroles by using tBuOOH as an oxidant (Scheme 16.). 44 Li and Duan showed the same reaction with nickel catalyst. 45 Heterogeneous γ-MnO 2 -catalyzed oxidative amination of benzoxazoles was reported.…”

Section: ■ Introductionmentioning

confidence: 68%

Catalytic Methods for Aromatic C–H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules

2015

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Transformations of aromatic compounds into the corresponding amines, amides, and imides through carbon–hydrogen (C–H) bond functionalization represent one of the most step- and atom-economical methods for the synthesis of arylamine compounds. Because arylamines are privileged structures in materials- and biology-oriented functional molecules, the development of novel and efficient synthetic methods for aromatic C–H amination has received significant attention from a wide range of research fields including materials and pharmaceuticals. This review covers recent advances in catalytic aromatic C–H amination reactions. An array of recently developed new reactions are categorized by the nature of aromatic substrates: (1) 5-membered heteroarenes, (2) arenes having a nitrogen moiety in the molecule (intramolecular C–H amination), (3) arenes having a directing group, (4) simple arenes with excess amounts, and (5) simple arenes as the limiting reagents.

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“…From this point the synthesis of C-N or C-O by the activation of C-H bond is very important. Xin W. and co-worker [72] synthesis new heterocyclic by the amination of five member heterocyclic ring with Metal or organocatalysis. To optimize the reaction of 2-Acetylfuran 10 (0.5 mmol) and saccharin (2.0 equiv) as substrates, under atmospheric conditions in the presence of CuCl (10 mol%) and select Fluor (2.0 equiv) at 120 o C for 6 h with nitro methane (CH3NO2) as the solvent, the desired imidation product 1-(5-aminofuran-2-yl)ethanone 11 was obtained in 55 % yield (Table 1, entry 1).…”

Section: Heterocyclic C-n Bonds Formationmentioning

confidence: 99%

Review for metal and organocatalysis of heterocyclic C-H functionalization

El‐Sayed¹,

Khaireldin²,

Elhefny³

2021

World J. Adv. Res. Rev.

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Over the last few decades, signiﬁcant efforts have been put forth towards the C−H bond group functionalization by transition-metalcatalysis and organocatalysis. Several efficient strategies to convert C-H bond to other groups C-C, C-N, C-O bonds have been implemented. The most attractive C-H bond functionalization was the C-H heterocyclic compounds activation that is practical method in organic synthesis. The new C–C, C–N and C–O bond as formed from the C-H bond activation by two diverse ways metal catalysis and/or organocatalysis. The most important is the synthesis of new bioactive heterocyclic compounds by easy and less expensive materials. In this review, we will cover most of the syntheses of heterocyclic derivatives by the functionalization of C-H bond in metal and organocatalytic reagents.

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Regioselective CH Imidation of Five‐Membered Heterocyclic Compounds through a Metal Catalytic or Organocatalytic Approach

Cited by 30 publications

References 76 publications

Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics

Catalytic C–H Imidation of Aromatic Cores of Functional Molecules: Ligand-Accelerated Cu Catalysis and Application to Materials- and Biology-Oriented Aromatics

Catalytic Methods for Aromatic C–H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules

Review for metal and organocatalysis of heterocyclic C-H functionalization

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