Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway
[Display omitted] •The first example of Ni-catalyzed Minisci acylation reaction was developed.•This protocol avoids using external chemical oxidants.•A ligand-to-metal electron transfer process was observed. A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electro...
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| Vydáno v: | Journal of catalysis Ročník 381; s. 38 - 43 |
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| Médium: | Journal Article |
| Jazyk: | angličtina |
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01.01.2020
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| ISSN: | 0021-9517, 1090-2694 |
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| Abstract | [Display omitted]
•The first example of Ni-catalyzed Minisci acylation reaction was developed.•This protocol avoids using external chemical oxidants.•A ligand-to-metal electron transfer process was observed.
A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids has been developed. The reaction is performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric analysis disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals. |
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| AbstractList | A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids has been developed. The reaction is performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric analysis disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals. [Display omitted] •The first example of Ni-catalyzed Minisci acylation reaction was developed.•This protocol avoids using external chemical oxidants.•A ligand-to-metal electron transfer process was observed. A nickel-catalyzed electrochemical methodology for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids has been developed. The reaction is performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric analysis disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals. |
| Author | Xu, Kun Zeng, Cheng-Chu Ding, Hang |
| Author_xml | – sequence: 1 givenname: Hang surname: Ding fullname: Ding, Hang – sequence: 2 givenname: Kun orcidid: 0000-0002-0419-8822 surname: Xu fullname: Xu, Kun email: kunxu@bjut.edu.cn – sequence: 3 givenname: Cheng-Chu orcidid: 0000-0002-5659-291X surname: Zeng fullname: Zeng, Cheng-Chu email: zengcc@bjut.edu.cn |
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| Cites_doi | 10.1016/j.tet.2019.01.060 10.1016/j.tetlet.2019.01.039 10.1021/acs.orglett.8b00920 10.1002/slct.201800496 10.1039/C4RA05777E 10.1021/acs.chemrev.8b00782 10.1021/ol300195c 10.1016/j.jelechem.2015.12.051 10.1021/jacs.8b02834 10.1021/acscatal.7b01683 10.1002/chem.201402516 10.1021/acs.orglett.7b03559 10.1021/acs.orglett.7b02589 10.1021/acs.joc.9b00004 10.1039/c1md00134e 10.1021/np50024a010 10.1039/c3cs60464k 10.1039/C8QO00645H 10.1002/adsc.201800692 10.1021/acs.chemrev.7b00271 10.1016/j.electacta.2013.10.093 10.1021/jacs.7b13387 10.1021/np50042a021 10.1021/jo00008a050 10.1021/acs.orglett.8b02016 10.1021/jacs.7b11025 |
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| SubjectTerms | acylation catalysts catalytic activity electrochemistry electron transfer Electrosynthesis free radicals heterocyclic nitrogen compounds keto acids Minisci acylation reactions nickel Nickel-catalysis oxidants voltammetry α-Keto acid |
| Title | Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway |
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