Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides
An efficient and air-tolerant Ni-catalyzed denitrogenative cross-electrophile coupling of benzotriazinones with benzyl chlorides has been developed via liquid-assisted grinding by using Mn powders as reductant and DMF as assisting liquid in the presence of anhydrous calcium chloride. Scope and limit...
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MDPI AG
2025-02-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/5/1060 |
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| author | Xuanxuan Zhang Yingying Hong Gang Zou |
| author_facet | Xuanxuan Zhang Yingying Hong Gang Zou |
| author_sort | Xuanxuan Zhang |
| collection | DOAJ |
| description | An efficient and air-tolerant Ni-catalyzed denitrogenative cross-electrophile coupling of benzotriazinones with benzyl chlorides has been developed via liquid-assisted grinding by using Mn powders as reductant and DMF as assisting liquid in the presence of anhydrous calcium chloride. Scope and limitations of the protocol to access diarylmethanes have been demonstrated with more than 20 examples, showing acceptable tolerance to functional group and steric hindrance. Although electron-withdrawing substituents on benzotriazinone or benzyl counterparts decrease the yields significantly, a series of N-alkyl-2-benzylbenzamides, diarylmethanes bearing an ortho-carbamoyl aryl group, could be obtained in modest to good yields. |
| format | Article |
| id | doaj-art-b62bcf7902d8401bb4efdb21ae2e1379 |
| institution | DOAJ |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-02-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-b62bcf7902d8401bb4efdb21ae2e13792025-08-20T02:52:45ZengMDPI AGMolecules1420-30492025-02-01305106010.3390/molecules30051060Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl ChloridesXuanxuan Zhang0Yingying Hong1Gang Zou2School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, ChinaSchool of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, ChinaSchool of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Rd, Shanghai 200237, ChinaAn efficient and air-tolerant Ni-catalyzed denitrogenative cross-electrophile coupling of benzotriazinones with benzyl chlorides has been developed via liquid-assisted grinding by using Mn powders as reductant and DMF as assisting liquid in the presence of anhydrous calcium chloride. Scope and limitations of the protocol to access diarylmethanes have been demonstrated with more than 20 examples, showing acceptable tolerance to functional group and steric hindrance. Although electron-withdrawing substituents on benzotriazinone or benzyl counterparts decrease the yields significantly, a series of N-alkyl-2-benzylbenzamides, diarylmethanes bearing an ortho-carbamoyl aryl group, could be obtained in modest to good yields.https://www.mdpi.com/1420-3049/30/5/1060diarylmethanebenzotriazinonecross-electrophile couplingnickel catalysisbenzylation |
| spellingShingle | Xuanxuan Zhang Yingying Hong Gang Zou Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides Molecules diarylmethane benzotriazinone cross-electrophile coupling nickel catalysis benzylation |
| title | Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides |
| title_full | Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides |
| title_fullStr | Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides |
| title_full_unstemmed | Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides |
| title_short | Liquid-Assisted Grinding Enables Efficient Ni-Catalyzed, Mn-Mediated Denitrogenative Cross-Electrophile Coupling of Benzotriazinones with Benzyl Chlorides |
| title_sort | liquid assisted grinding enables efficient ni catalyzed mn mediated denitrogenative cross electrophile coupling of benzotriazinones with benzyl chlorides |
| topic | diarylmethane benzotriazinone cross-electrophile coupling nickel catalysis benzylation |
| url | https://www.mdpi.com/1420-3049/30/5/1060 |
| work_keys_str_mv | AT xuanxuanzhang liquidassistedgrindingenablesefficientnicatalyzedmnmediateddenitrogenativecrosselectrophilecouplingofbenzotriazinoneswithbenzylchlorides AT yingyinghong liquidassistedgrindingenablesefficientnicatalyzedmnmediateddenitrogenativecrosselectrophilecouplingofbenzotriazinoneswithbenzylchlorides AT gangzou liquidassistedgrindingenablesefficientnicatalyzedmnmediateddenitrogenativecrosselectrophilecouplingofbenzotriazinoneswithbenzylchlorides |