(Diacetoxy)iodobenzene-Mediated Oxidative C–H Amination of Imidazopyridines at Ambient Temperature

Mondal, Susmita; Samanta, Sadhanendu; Jana, Sourav; Hajra, Alakananda

doi:10.1021/acs.joc.7b00564

Cited by 80 publications

(21 citation statements)

References 46 publications

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“…However, C−N bond formation reactions of C3 position based on the oxidative cross coupling of C−H and N−H bonds have been less developed. In 2017, the group of Hajra reported the hypervalent iodine‐mediated oxidative C−H amination of imidazopyridines with secondary alkyl amine. In the same year, Sun and coworkers developed the visible light‐induced C3‐sulfonamidation of imidazopyridines with sulfamides.…”

Section: Methodsmentioning

confidence: 99%

Electrochemical C−H/N−H Oxidative Cross Coupling of Imidazopyridines with Diarylamines to Synthesize Triarylamine Derivatives

Liu

Deng

et al. 2019

ChemElectroChem

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An electrochemical dehydrogenative C−H/N−H cross coupling of imidazopyridines with diarylamines has been developed. A variety of triarylamine derivatives could be obtained in high regioselectivities and moderate‐to‐good yields. In this transformation, the reaction is conducted in a simple undivided cell without using a metal catalyst or a stoichiometric amount of external chemical oxidants. Mechanistic studies indicate that the C−N bond is likely to be formed through the cross coupling between an arene cation radical and a nitrogen radical.

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Section: Methodsmentioning

confidence: 99%

Electrochemical C−H/N−H Oxidative Cross Coupling of Imidazopyridines with Diarylamines to Synthesize Triarylamine Derivatives

Liu

Deng

et al. 2019

ChemElectroChem

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“…Hazra and co-workers explored a PIDA-mediated C3-amination of imidazo[1,2-a]pyridines 1 with cyclic secondary amines 62 to synthesize respective aminated products 63 in 59-86% yields (Scheme 40). [62] This protocol is metal-free and utilizes morpholine, thiomorpholine and piperidine as an amine source (62) and PIDA as an oxidant. Other oxidants such as (bis (trifluoroacetoxy)iodo)benzene (PIFA), K 2 S 2 O 8 , and TBHP did not produce the respective product.…”

Section: Aminationmentioning

confidence: 99%

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

et al. 2020

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Direct CÀ H bond functionalization through radical pathway has emerged as a powerful and ideal strategy for the synthesis of organic compounds. This review provides an overview of recent developments in radical CÀ H functionalization of imidazoheterocycles such as imidazo[1,2-a] pyridine, benzo[d]imidazo[2,1-b]thiazole, imidazo [2,1-b]thiazole, imidazo[1,2-a]pyrimidine, imidazo [2,1-a]isoquinoline, imidazo[1,2-a]pyrazine and imidazo[1,2-a]quinoline using organic peroxides, photo/electric-induced protocols, iodine-based reagents, first-row transition metal catalysts (Fe, Mn, Ni and Cu) and inorganic oxidants/or

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“…[6] However, few reports are available for the expeditious synthesis of these molecules via direct incorporation of amine or amine derivatives to a carbon atom through the formation of C-N bond under transition metal-free conditions. [7] In 2017, Hajra group [8] achieved the PIDA-mediated direct oxidative C-H amination of imidazopyridines under transition metal-free conditions at room temperature. This methodology has broad substrate scopes and provides the corresponding 3-amino substituted imidazopyridines in moderate to high yields in short reaction times.…”

Section: C-h Amination Of Imidazole-fused Heterocyclesmentioning

confidence: 99%

Recent Progress in Transition Metal-Free C-Heteroatom Bond Formation by Functionalization of C-H Bond in Imidazole-Fused Heterocycles

Xu¹,

Chen²,

Wang³

2019

Chin. J. Org. Chem.

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Recently, the direct incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization has rapidly been advanced and become an eco-friendly synthetic tool for the synthesis of functionalized natural or bioactive molecules such as (hetero)arenes, olefins, carbonyl compounds. In particular, the C-H functionalization of imidazole-fused heterocycles has been considered to be the most important since it can lead to a new class of biologically active compounds. The recent progress in the incorporation of heteroatom into imidazole-fused heterocycles through transition metal-free C-H functionalization is introduced, and their mechanisms from a new perspective are also elaborated.

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(Diacetoxy)iodobenzene-Mediated Oxidative C–H Amination of Imidazopyridines at Ambient Temperature

Cited by 80 publications

References 46 publications

Electrochemical C−H/N−H Oxidative Cross Coupling of Imidazopyridines with Diarylamines to Synthesize Triarylamine Derivatives

Electrochemical C−H/N−H Oxidative Cross Coupling of Imidazopyridines with Diarylamines to Synthesize Triarylamine Derivatives

Recent Advances in Radical C−H Bond Functionalization of Imidazoheterocycles

Recent Progress in Transition Metal-Free C-Heteroatom Bond Formation by Functionalization of C-H Bond in Imidazole-Fused Heterocycles

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