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Iron-catalyzed C-H bond functionalization into oxime ethers via photo-induced ligand-to-metal charge transfer SCIE
期刊论文 | 2025 | ORGANIC & BIOMOLECULAR CHEMISTRY
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Abstract :

We have developed a novel strategy for Fe-catalyzed C-H functionalization into oxime ethers through photo-induced ligand-to-metal charge transfer (LMCT). The method avoids the need for photocatalysts and bases, utilizing a cheap and readily available catalyst under mild conditions. It offers a broad substrate scope, scalability, and high efficiency, providing a promising and cost-effective strategy for synthesizing oxime ethers from simple and abundant starting materials.

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GB/T 7714 Hao, Zhijun , Han, Jianguo , Liu, Xiushan et al. Iron-catalyzed C-H bond functionalization into oxime ethers via photo-induced ligand-to-metal charge transfer [J]. | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 .
MLA Hao, Zhijun et al. "Iron-catalyzed C-H bond functionalization into oxime ethers via photo-induced ligand-to-metal charge transfer" . | ORGANIC & BIOMOLECULAR CHEMISTRY (2025) .
APA Hao, Zhijun , Han, Jianguo , Liu, Xiushan , Yue, Huifeng . Iron-catalyzed C-H bond functionalization into oxime ethers via photo-induced ligand-to-metal charge transfer . | ORGANIC & BIOMOLECULAR CHEMISTRY , 2025 .
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Iron-catalyzed C-H bond functionalization into oxime ethers via photo-induced ligand-to-metal charge transfer Scopus
期刊论文 | 2025 | Organic and Biomolecular Chemistry
Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes SCIE
期刊论文 | 2024 , 60 (39) , 5153-5156 | CHEMICAL COMMUNICATIONS
WoS CC Cited Count: 2
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Abstract :

We have developed a novel Ni-catalyzed reductive cross-coupling reaction of aryl bromides and alkyl iodides via a photoactive electron donor-acceptor (EDA) complex. This photo-induced process enables the efficient construction of C(sp(2))-C(sp(3)) bonds in the absence of an external photocatalyst. Electronically and structurally diverse aryl bromides, as well as secondary and primary alkyl iodides could undergo this transformation smoothly. Natural product derivatives were employed successfully, and UV-vis spectroscopy was utilized to gain mechanistic insight.

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GB/T 7714 Alsharif, Salman , Zhu, Chen , Liu, Xiushan et al. Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes [J]. | CHEMICAL COMMUNICATIONS , 2024 , 60 (39) : 5153-5156 .
MLA Alsharif, Salman et al. "Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes" . | CHEMICAL COMMUNICATIONS 60 . 39 (2024) : 5153-5156 .
APA Alsharif, Salman , Zhu, Chen , Liu, Xiushan , Lee, Shao-Chi , Yue, Huifeng , Rueping, Magnus . Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes . | CHEMICAL COMMUNICATIONS , 2024 , 60 (39) , 5153-5156 .
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Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes Scopus
期刊论文 | 2024 , 60 (39) , 5153-5156 | Chemical Communications
Nickel-catalyzed C(sp2)-C(sp3) coupling via photoactive electron donor-acceptor complexes EI
期刊论文 | 2024 , 60 (39) , 5153-5156 | Chemical Communications
Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis SCIE
期刊论文 | 2024 , 30 (23) | CHEMISTRY-A EUROPEAN JOURNAL
WoS CC Cited Count: 2
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Abstract :

A new cross-coupling of trifluoromethyl arenes has been realized via multiphoton photoredox catalysis. Trifluoromethyl arenes were demonstrated to undergo selective mono-defluorinative alkylation under mild reaction conditions providing access to a series of valuable alpha,alpha-difluorobenzylic compounds. The reaction shows broad substrate scope and general functional group tolerance. In addition to the electron-deficient trifluoromethyl arenes that are easily reduced to the corresponding radical anion, more challenging electron-rich substrates were also successfully applied. Steady-State Stern-Volmer quenching studies indicated that the trifluoromethyl arenes were reduced by the multiphoton excited Ir-based photocatalyst. A new cross-coupling of trifluoromethyl arenes has been realized via multiphoton photoredox catalysis. A series of valuable alpha,alpha-difluorobenzylic compounds can be generated while the the addition of D2O leads to highly deuterated derivatives.+ image

Keyword :

alkylation alkylation defluorination defluorination fluorination fluorination multi photon catalysis multi photon catalysis photoredox catalysis photoredox catalysis

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GB/T 7714 Jia, Jiaqi , Zhumagazy, Serik , Zhu, Chen et al. Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis [J]. | CHEMISTRY-A EUROPEAN JOURNAL , 2024 , 30 (23) .
MLA Jia, Jiaqi et al. "Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis" . | CHEMISTRY-A EUROPEAN JOURNAL 30 . 23 (2024) .
APA Jia, Jiaqi , Zhumagazy, Serik , Zhu, Chen , Lee, Shao-Chi , Alsharif, Salman , Yue, Huifeng et al. Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis . | CHEMISTRY-A EUROPEAN JOURNAL , 2024 , 30 (23) .
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Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis Scopus
期刊论文 | 2024 , 30 (23) | Chemistry - A European Journal
Selective Mono-Defluorinative Cross-Coupling of Trifluoromethyl arenes via Multiphoton Photoredox Catalysis EI
期刊论文 | 2024 , 30 (23) | Chemistry - A European Journal
Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions SCIE
期刊论文 | 2024 , 63 (51) | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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Abstract :

Bicyclo[1.1.1]pentane (BCP), recognized as a bioisostere for para-disubstituted benzene, has gained widespread interest in drug development due to its ability to enhance the physicochemical properties of pharmaceuticals. In this work, we introduce a photoinduced, halogen bonding-initiated, metal-free strategy for synthesizing various BCP derivatives. This method involves the generation of nucleophilic alpha-aminoalkyl radicals via halogen-bonding adducts. These undergo selective radical addition to [1.1.1]propellane, yielding electrophilic BCP radicals that subsequently participate in polarity-matched additions, culminating in the difunctionalization of bicyclopentane. The versatility and practicality of this metal-free approach are underscored by its broad substrate scope, which includes late-stage functionalization and a series of valuable transformations, all conducted under mild reaction conditions.

Keyword :

[1.1.1]Propellane [1.1.1]Propellane Difunctionalization Difunctionalization Halogen bond Halogen bond Polarity-match Polarity-match XAT XAT

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GB/T 7714 Yi, Liang , Kong, Deshen , Kale, Ajit Prabhakar et al. Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (51) .
MLA Yi, Liang et al. "Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 63 . 51 (2024) .
APA Yi, Liang , Kong, Deshen , Kale, Ajit Prabhakar , Alshehri, Rawan , Yue, Huifeng , Gizatullin, Amir et al. Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2024 , 63 (51) .
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Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions Scopus
期刊论文 | 2024 , 63 (51) | Angewandte Chemie - International Edition
Halogen Bonding Initiated Difunctionalization of [1.1.1]Propellane via Photoinduced Polarity Match Additions EI
期刊论文 | 2024 , 63 (51) | Angewandte Chemie - International Edition
Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes Scopus
期刊论文 | 2023 , 2 (11) , 1068-1081 | Nature Synthesis
SCOPUS Cited Count: 10
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Abstract :

The development of general and efficient strategies for the construction of allenes is important due to their wide applications. Although few protocols have been developed via the 1,4-difunctionalization of 1,3-enynes under thermal or photoredox conditions, the mild and robust methodology for dicarbofunctionalization and hydroalkylation remains unexplored. In the present study, we report an electrochemical multicomponent protocol for the chemo- and regioselective difunctionalization of 1,3-enynes. In particular, 1,4-arylalkylation and unsymmetrical dialkylation have been realized via electro- and nickel dual catalysis using graphite/nickel foam and zinc/nickel foam as electrodes, respectively. The use of a Zn/reticulated vitreous carbon electrode led to efficient 1,4-hydro(deutero)alkylation in the absence of a metal catalyst. A wide range of structurally diverse tri- and tetra-substituted allenes were easily prepared with good efficiency and excellent regioselectivity under mild reaction conditions. Notably, a series of natural product- and drug-derived substrates could undergo late-stage functionalization to generate the corresponding complex allenes. [Figure not available: see fulltext.]. © 2023, The Author(s), under exclusive licence to Springer Nature Limited.

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GB/T 7714 Zhu, C. , Chen, H. , Yue, H. et al. Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes [J]. | Nature Synthesis , 2023 , 2 (11) : 1068-1081 .
MLA Zhu, C. et al. "Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes" . | Nature Synthesis 2 . 11 (2023) : 1068-1081 .
APA Zhu, C. , Chen, H. , Yue, H. , Rueping, M. . Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes . | Nature Synthesis , 2023 , 2 (11) , 1068-1081 .
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Electrochemical chemo- and regioselective arylalkylation, dialkylation and hydro(deutero)alkylation of 1,3-enynes ESCI
期刊论文 | 2023 , 2 (11) , 1068-1081 | NATURE SYNTHESIS
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