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学者姓名：岳会锋
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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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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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The difunctionalization of unsaturated bonds plays a vital role in the enrichment of molecular complexity. While various catalytic methods for alkene and alkyne difunctionalization have been developed in recent years, hetero-functionalization the introduction of two different atoms has been less explored. This is mainly due to the challenges associated with achieving high chemo-, regio-, and stereoselectivity, especially when adding two similar atoms from the same group across unsaturated bonds. In this study, we describe a nickel-catalyzed, three-component reductive protocol for group 14 element hetero-difunctionalization of 1,3-enynes using electrochemistry. This new method is mild, selective, and general, allowing for the silyl-, germanyl-, and stannyl-alkylation of enynes. Various chlorosilanes as well as chlorogermans, and chlorostannanes can be successfully used in combination with aryl/alkyl-substituted 1,3-enynes and primary, secondary, and tertiary alkyl bromides in the electroreductive coupling.
Keyword ：
1 1 3-Enynes 3-Enynes Alkyl Halides Alkyl Halides Chlorosilanes Chlorosilanes Electrochemistry Electrochemistry Nickel Nickel
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| GB/T 7714 | Chen, Haifeng , Zhu, Chen , Yue, Huifeng et al. Group 14 Elements Hetero-Difunctionalizations via Nickel-Catalyzed Electroreductive Cross-Coupling [J]. | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2023 , 62 (33) . |
| MLA | Chen, Haifeng et al. "Group 14 Elements Hetero-Difunctionalizations via Nickel-Catalyzed Electroreductive Cross-Coupling" . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62 . 33 (2023) . |
| APA | Chen, Haifeng , Zhu, Chen , Yue, Huifeng , Rueping, Magnus . Group 14 Elements Hetero-Difunctionalizations via Nickel-Catalyzed Electroreductive Cross-Coupling . | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION , 2023 , 62 (33) . |
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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. The synthesis of allenes through 1,4-difunctionalization of 1,3-enynes typically requires preformed organometallic species, high temperature or specific alkyl radical precursors. Now an electrochemical multicomponent protocol for the chemo- and regioselective 1,4-difunctionalization of 1,3-enynes is reported, which uses alkyl bromides with aryl bromides, alkyl bromides or H2O/D2O as reagents for 1,4-difunctionalization.
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| GB/T 7714 | Zhu, Chen , Chen, Haifeng , Yue, Huifeng 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, Chen 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, Chen , Chen, Haifeng , Yue, Huifeng , Rueping, Magnus . 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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| GB/T 7714 | Yue, Huifeng , Zhu, Chen , Rueping, Magnus . Electrochemical cobalt catalysis enabled construction of diverse chiral skeletons via C-H activation [J]. | SCIENCE BULLETIN , 2023 , 68 (16) : 1730-1732 . |
| MLA | Yue, Huifeng et al. "Electrochemical cobalt catalysis enabled construction of diverse chiral skeletons via C-H activation" . | SCIENCE BULLETIN 68 . 16 (2023) : 1730-1732 . |
| APA | Yue, Huifeng , Zhu, Chen , Rueping, Magnus . Electrochemical cobalt catalysis enabled construction of diverse chiral skeletons via C-H activation . | SCIENCE BULLETIN , 2023 , 68 (16) , 1730-1732 . |
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Abstract ：
Photoinduced nickel-catalyzed demethylative cyanation and decarboxylative cyanomethylation of aryl halides are described here. Commercially available bromoacetonitrile was found to act as an efficient cyanating reagent for the photoinduced cyanation reaction in the absence of a photocatalyst. Moreover, photoredox and nickel dual-catalyzed decarboxylative cyanomethylation of aryl halides has also been realized using cesium cyanoacetate under mild conditions. A series of aryl and benzyl nitriles bearing diverse functional groups were prepared with good to high efficiency.
Keyword ：
aryl halides aryl halides cyanation cyanation cyanomethylation cyanomethylation nickel nickel photocatalysis photocatalysis
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| GB/T 7714 | Lee, Shao-Chi , Zhu, Chen , Huang, Kun et al. Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides [J]. | ACS CATALYSIS , 2023 , 13 (24) : 16279-16285 . |
| MLA | Lee, Shao-Chi et al. "Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides" . | ACS CATALYSIS 13 . 24 (2023) : 16279-16285 . |
| APA | Lee, Shao-Chi , Zhu, Chen , Huang, Kun , Bau, Jeremy A. , Jia, Jiaqi , Yue, Huifeng et al. Photoinduced Nickel-Catalyzed Demethylative Cyanation and Decarboxylative Cyanomethylation of Aryl Halides . | ACS CATALYSIS , 2023 , 13 (24) , 16279-16285 . |
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