Regioselective intramolecular sp<sup>2</sup> C–H amination: direct <i>vs.</i> mediated electrooxidation

Shi, Jianxue; Li, Jingjing; Zhao, Wenjing; Cui, Mengru; Ni, Wanying; Li, Lijun; Liu, Wenmin; Xu, Kun; Zhang, Sheng

doi:10.1039/d0qo01584a

Cited by 19 publications

(16 citation statements)

References 34 publications

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“…Shi et al 69 reported the synthesis of benzimidazole-fused phenanthridine via intramolecular C–H amination under electrochemical conditions. They carried out the C–H amination reaction mediated by triarylamine as well as by direct electro-oxidation.…”

Section: Transition Metal-free Reactionsmentioning

confidence: 99%

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

et al. 2022

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Section: Transition Metal-free Reactionsmentioning

confidence: 99%

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

et al. 2022

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“…The classic methods for the synthesis of benzimidazole-fused phenanthridines relied on the Pd catalysis or hypervalent iodine oxidation reactions. In 2021, Xu, Zhang and co-workers report a triarylamine-mediated electrochemical protocol for the formation of benzimidazole-fused phenanthridines in good to excellent yields ( Shi et al, 2021 ) ( Scheme 4 ). The reaction was carried out in an undivided cell with carbon cloth as the anode and platinum as the cathode under CCE conditions.…”

Section: Intramolecular Electrochemical C(sp 2 )-H...mentioning

confidence: 99%

Metal-Free Synthesis of N-Heterocycles via Intramolecular Electrochemical C-H Aminations

Wang

Zheng

et al. 2022

Front. Chem.

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N-heterocycles are key structural units in many drugs, biologically interesting molecules and functional materials. To avoid the residues of metal catalysts, the construction of N-heterocycles under metal-free conditions has attracted much research attention in academia and industry. Among them, the intramolecular electrochemical C-H aminations arguably constitute environmentally friendly methodologies for the metal-free construction of N-heterocycles, mainly due to the direct use of clean electricity as the redox agents. With the recent renaissance of organic electrosynthesis, the intramolecular electrochemical C-H aminations have undergone much progress in recent years. In this article, we would like to summarize the advances in this research field since 2019. The emphasis is placed on the reaction design and mechanistic insight. The challenges and future developments in the intramolecular electrochemical C-H aminations are also discussed.

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“…Also, cross dehydrohalogenative C–N coupling reactions toward intramolecular photocyclization of phenanthro[9,10-d]imidazoles and 8-aryloxy benzo[ e ][1,2,4]triazines for the construction of N -heterocycles was documented. Similarly, intramolecular C–H amination reactions are known for the synthesis of heterocycles via an electrochemical method. , Instead, in traditional photochemistry, no direct dehydrogenative coupling is known.…”

Section: Introductionmentioning

confidence: 99%

“…Similarly, intramolecular C−H amination reactions are known for the synthesis of heterocycles via an electrochemical method. 28,29 Instead, in traditional photochemistry, no direct dehydrogenative coupling is known.…”

Section: ■ Introductionmentioning

confidence: 99%

A Photochemical Intramolecular C–N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines

et al. 2021

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Herein, we report a direct photochemical dehydrogenative C–N coupling of unactivated C(sp2)–H and N(sp2)–H bonds. The catalysts or additive-free transformation of 2-([1,1′-biphenyl]-2-yl)-1H-benzo[d]imidazole to benzo[4,5]imidazo[1,2-f]phenanthridine was achieved at ∼350 nm of irradiation via ε-hydrogen abstraction. DFT calculations helped to understand that the N–H···π interaction was essential for the reaction to proceed at a lower energy than expected.

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Regioselective intramolecular sp² C–H amination: direct vs. mediated electrooxidation

Abstract: We reported an electrochemical intramolecular C-H amination approach to construct benzimidazole-fused phenanthridines. This electrochemical approach was compatible with variety of functional groups, including ester, silyl, thioether, pyridyl, amine groups. With...

Cited by 19 publications

References 34 publications

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Metal-Free Synthesis of N-Heterocycles via Intramolecular Electrochemical C-H Aminations

A Photochemical Intramolecular C–N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines

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Regioselective intramolecular sp2 C–H amination: direct vs. mediated electrooxidation

Abstract: We reported an electrochemical intramolecular C-H amination approach to construct benzimidazole-fused phenanthridines. This electrochemical approach was compatible with variety of functional groups, including ester, silyl, thioether, pyridyl, amine groups. With...

Cited by 19 publications

References 34 publications

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Electro-organic synthesis: an environmentally benign alternative for heterocycle synthesis

Metal-Free Synthesis of N-Heterocycles via Intramolecular Electrochemical C-H Aminations

A Photochemical Intramolecular C–N Coupling Toward the Synthesis of Benzimidazole-Fused Phenanthridines

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Regioselective intramolecular sp² C–H amination: direct vs. mediated electrooxidation