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

Liu, Kun; Wu, Jiarong; Deng, Yuqi; Song, Chunlan; Song, Wenxu; Lei, Aiwen

doi:10.1002/celc.201900138

Cited by 32 publications

(23 citation statements)

References 74 publications

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“…b) Aromatic C−H imidation via electrochemical oxidation [207] . c) C−H amination of imidazopyridines with diarylamines through anodic oxidation [208] . d) Electrochemical cross‐coupling reaction between electron‐rich arenes and diarylamines [209] .…”

Section: C‐centered Radicalsmentioning

confidence: 99%

“…Further radical addition of ( 380 ) to the arene ( 377 ) and a second oxidation generates carbocation ( 382 ), which is finally rearomatized to furnish the final product. A related approach for direct C−H amination of imidazpyridines ( 383 ) with diarylamines ( 384 ) through anodic oxidation (Scheme 43c) was studied [208] . For this reaction, the anodic generation of the diarylaminyl radical ( 387 ) is proposed as well as a delocalized radical‐cation ( 386 ) from the corresponding starting molecules.…”

Section: N‐centered Radicalsmentioning

confidence: 99%

See 1 more Smart Citation

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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During the last decade several research groups have been developing electrochemical procedures to access highly functionalized organic molecules. Among the most exciting advances, the possibility of using free radical chemistry has attracted the attention of the most important synthetic groups. Nowadays, electrochemical strategies based on these species with a synthetic purpose are published continuously in scientific journals, increasing the alternatives for the synthetic organic chemistry laboratories. Free radicals can be obtained in organic electrochemical reactions; thus, this review reassembles the last decade's (2010–2020) efforts of the electrosynthetic community to generate and take advantage of the C‐, O‐, and N‐centered radicals’ reactivity. The electrochemical reactions that occur, as well as the proposed mechanism, are discussed, trying to give clear information about the used conditions and reactivity of these reactive intermediate species.

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Section: C‐centered Radicalsmentioning

confidence: 99%

Section: N‐centered Radicalsmentioning

confidence: 99%

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Chicas-Baños

Frontana‐Uribe

2021

The Chemical Record

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“…Recently, Lei group [11] presented an effective electrochemical system for the direct C-H amination of imidazopyridines with diarylamines in a simple undivided cell without using metal catalyst or stoichiometric amount of external chemical oxidants. This protocol provided a simple and efficient way to access a variety of heterocycles containing triarylamines under transition metal-free conditions.…”

Section: Scheme 3 Visible Light Induced Amination Of Imidazopyridinesmentioning

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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“…Electrochemical oxidation of diarylamines is of special interest as a "greener" alternative to chemical oxidation. [10][11][12][13][14][15] Electrochemical oxidation of diarylamines can follow various reaction paths, as determined by the structure of amines and reaction conditions. Meanwhile, the number of reports on diarylamines electrooxidation is still rather limited.…”

Section: Introductionmentioning

confidence: 99%

Regio‐ and Chemoselectivity of Oxidative Conversion of Diarylamines to N,N’‐Diaryldihydrophenazines and N,N’‐Diarylbenzidines: DFT and Experimental Study

et al. 2021

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Detailed quantum-chemical investigation of competing routes of substituted diphenylamines oxidation was performed. Chemoselectivity as well regioselectivity of the phenazine and benzidine skeletons formation were elucidated and confirmed by experimental testing on the model diphenylamines containing CF 3 , Bu t , α-methylcyclopropyl substituents. It was shown that the oxidation of 4,4'-disubstituted donor-acceptor amines leads to dihydrophenazines chemo-and regioselectively. For 2,4'-disubstituted donor-acceptor diphenylamines, the reaction rates for the competing reactions differ ca. 25 times in favor of the benzidine formation. Oxidation of 2,4'-disubstituted diphenylamines with electron-rich phenyl rings is much less selective; both benzidines and dihydrophenazines are formed. It was shown that the activation energy for the benzidines formation is strongly dependent on the electronic properties of the substituents in the starting amine, in contrast to the competing formation of the phenazines, which is more sensitive to sterical bulkiness of substituents.

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

Cited by 32 publications

References 74 publications

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

Electrochemical Generation and Use in Organic Synthesis of C‐, O‐, and N‐Centered Radicals

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

Regio‐ and Chemoselectivity of Oxidative Conversion of Diarylamines to N,N’‐Diaryldihydrophenazines and N,N’‐Diarylbenzidines: DFT and Experimental Study

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