Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

Wang, Shijun; Wang, Long; Tang, Xiang‐Ying

doi:10.1016/j.isci.2023.106528

iScience

2023

DOI: 10.1016/j.isci.2023.106528

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Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

Shijun Wang¹,

Long Wang²,

Xiang‐Ying Tang³

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Cited by 4 publications

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Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

Dixit,

Pooja,

Jain

2023

Adv Synth Catal

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Abstract. We demonstrate a photocatalyst and transition metal catalyst free photo‐activation of quinoxalin‐2(1H)‐ones in visible light in the presence of an acid catalyst. The photoactivated quinoxalin‐2(1H)‐one species transfers its energy to oxygen which promotes C‐N cross dehydrogenative coupling with nucleophilic partners such as carbazoles, azoles and amides giving the products in 42‐75% yields. Preliminary studies reveal quinoxalin‐2(1H)‐one‐carbazole adducts to display fluorescent properties including Intramolecular Charge Transfer (ICT) and Aggregate Induced Emission (AIE).

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Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

Dixit,

Pooja,

Jain

2023

Adv Synth Catal

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B(C₆F₅)₃‐Catalyzed N‐Allylation of Hydrazines with Allylic Alcohols

Xu,

Yang,

Yao

et al. 2024

Adv Synth Catal

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A N‐allylation of monosubstituted acyl hydrazines with allylic alcohols has been developed by using B(C6F5)3 catalysis. This protocol allows for convenient access to various synthetically useful N‐allylated hydrazine products in 48‐96% yields with broad substrate scope and wide functional group compatibility. The operationally simple reaction proceeds without calling for stringent removal of air and moisture, and can be readily scaled up to gram scale. Preliminary mechanistic studies support that the generation of an allylic carboncation is involved in the catalytic cycle, and the reaction proceeds via the in situ formation of diallyl ethers as intermediates.

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Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP–B(C₆F₅)₃ adduct

Li,

Zhu,

Gong

et al. 2024

Green Chem.

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Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

Cited by 4 publications

References 68 publications

Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

B(C₆F₅)₃‐Catalyzed N‐Allylation of Hydrazines with Allylic Alcohols

Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP–B(C₆F₅)₃ adduct

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Synergistic effect of hydrogen bonds and π-π interactions of B(C6F5)3·H2O/amides complex: Application in photoredox catalysis

Cited by 4 publications

References 68 publications

Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

Visible Light‐Mediated, Acid‐Catalyzed, C−N Cross Dehydrogenative Coupling of Quinoxalin‐2(1H)‐ones with Carbazoles and Amides: Access to Fluorescent Probes Featuring Aggregate Induced Emission

B(C6F5)3‐Catalyzed N‐Allylation of Hydrazines with Allylic Alcohols

Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP–B(C6F5)3 adduct

Contact Info

Product

Resources

About

B(C₆F₅)₃‐Catalyzed N‐Allylation of Hydrazines with Allylic Alcohols

Green and controllable synthesis of symmetrical and unsymmetrical difluoromethylated diarylmethanes via a direct bisarylation strategy enabled by an HFIP–B(C₆F₅)₃ adduct