Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts
Amines are abundant in natural product chemistry and are readily available chemical raw materials. The C-N bonds of amines are difficult to break due to the large C-N bond energy. In recent years, chemists have developed a variety of activation methods for amino groups of amines. Among these reporte...
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| Format: | Article |
| Language: | English |
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AIMS Press
2023-07-01
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| Series: | AIMS Molecular Science |
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| Online Access: | https://www.aimspress.com/article/doi/10.3934/molsci.2023011?viewType=HTML |
| _version_ | 1797656206569897984 |
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| author | Qingle Zeng Fuhai Li Xianjie Yin |
| author_facet | Qingle Zeng Fuhai Li Xianjie Yin |
| author_sort | Qingle Zeng |
| collection | DOAJ |
| description | Amines are abundant in natural product chemistry and are readily available chemical raw materials. The C-N bonds of amines are difficult to break due to the large C-N bond energy. In recent years, chemists have developed a variety of activation methods for amino groups of amines. Among these reported methods, to convert amines into quaternary ammonium salts is preferred, for quaternary ammonium salts are readily available and stable. In recent years, great progress has been achieved in the study of transition metal-catalyzed construction of various C-X bonds involving aromatic amines and benzyl amines-derived quaternary ammonium salts by cleavage of C-N bonds. This review describes the transition metal-catalyzed reaction of quaternary ammonium salts to construct C-X bonds by cleavage of C-N bond. Moreover, if chiral benzylamines-derived quaternary ammonium salts are used, a variety of highly enantiomeric pure chiral organic compounds can also be obtained. The chirality of quaternary ammonium salts remained good in the products and all reactions underwent S<sub>N</sub>2-type configuration inversion. |
| first_indexed | 2024-03-11T17:26:03Z |
| format | Article |
| id | doaj.art-bd6aa5a7714a4acd818e71e6440b6de0 |
| institution | Directory Open Access Journal |
| issn | 2372-0301 |
| language | English |
| last_indexed | 2024-03-11T17:26:03Z |
| publishDate | 2023-07-01 |
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| series | AIMS Molecular Science |
| spelling | doaj.art-bd6aa5a7714a4acd818e71e6440b6de02023-10-19T00:55:30ZengAIMS PressAIMS Molecular Science2372-03012023-07-0110315317010.3934/molsci.2023011Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium saltsQingle Zeng0Fuhai Li 1Xianjie Yin2College of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, ChinaCollege of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, ChinaCollege of Materials, Chemistry & Chemical Engineering, Chengdu University of Technology, Chengdu 610059, ChinaAmines are abundant in natural product chemistry and are readily available chemical raw materials. The C-N bonds of amines are difficult to break due to the large C-N bond energy. In recent years, chemists have developed a variety of activation methods for amino groups of amines. Among these reported methods, to convert amines into quaternary ammonium salts is preferred, for quaternary ammonium salts are readily available and stable. In recent years, great progress has been achieved in the study of transition metal-catalyzed construction of various C-X bonds involving aromatic amines and benzyl amines-derived quaternary ammonium salts by cleavage of C-N bonds. This review describes the transition metal-catalyzed reaction of quaternary ammonium salts to construct C-X bonds by cleavage of C-N bond. Moreover, if chiral benzylamines-derived quaternary ammonium salts are used, a variety of highly enantiomeric pure chiral organic compounds can also be obtained. The chirality of quaternary ammonium salts remained good in the products and all reactions underwent S<sub>N</sub>2-type configuration inversion.https://www.aimspress.com/article/doi/10.3934/molsci.2023011?viewType=HTMLtransition metal catalysisaminesquaternary ammonium saltscleavage of c-n bondconstruction of c-x bonds |
| spellingShingle | Qingle Zeng Fuhai Li Xianjie Yin Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts AIMS Molecular Science transition metal catalysis amines quaternary ammonium salts cleavage of c-n bond construction of c-x bonds |
| title | Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts |
| title_full | Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts |
| title_fullStr | Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts |
| title_full_unstemmed | Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts |
| title_short | Transition metal-catalyzed construction of C-X bonds via cleavage of C-N bond of quaternary ammonium salts |
| title_sort | transition metal catalyzed construction of c x bonds via cleavage of c n bond of quaternary ammonium salts |
| topic | transition metal catalysis amines quaternary ammonium salts cleavage of c-n bond construction of c-x bonds |
| url | https://www.aimspress.com/article/doi/10.3934/molsci.2023011?viewType=HTML |
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