Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions
Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of <i>N</i>-acylazetidines using the electri...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/3/459 |
| _version_ | 1818910860065636352 |
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| author | Hengzhao Li Zemin Lai Adila Adijiang Hongye Zhao Jie An |
| author_facet | Hengzhao Li Zemin Lai Adila Adijiang Hongye Zhao Jie An |
| author_sort | Hengzhao Li |
| collection | DOAJ |
| description | Functionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of <i>N</i>-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides. |
| first_indexed | 2024-12-19T22:49:31Z |
| format | Article |
| id | doaj.art-88b249bf63954588b4c4ed7d3b2e98ca |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T22:49:31Z |
| publishDate | 2019-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-88b249bf63954588b4c4ed7d3b2e98ca2022-12-21T20:02:51ZengMDPI AGMolecules1420-30492019-01-0124345910.3390/molecules24030459molecules24030459Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free ConditionsHengzhao Li0Zemin Lai1Adila Adijiang2Hongye Zhao3Jie An4College of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, ChinaCollege of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, ChinaCollege of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, ChinaCollege of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, ChinaCollege of Science, China Agricultural University, No. 2 Yuanmingyuan West Road, Beijing 100193, ChinaFunctionalization of amide bond via the cleavage of a non-carbonyl, C-N σ bond remains under-investigated. In this work, a transition-metal-free single-electron transfer reaction has been developed for the C-N σ bond cleavage of <i>N</i>-acylazetidines using the electride derived from sodium dispersions and 15-crown-5. Of note, less strained cyclic amides and acyclic amides are stable under the reaction conditions, which features the excellent chemoselectivity of the reaction. This method is amenable to a range of unhindered and sterically encumbered azetidinyl amides.https://www.mdpi.com/1420-3049/24/3/459amidesC-N σ bond cleavagesodiumcrown ether |
| spellingShingle | Hengzhao Li Zemin Lai Adila Adijiang Hongye Zhao Jie An Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions Molecules amides C-N σ bond cleavage sodium crown ether |
| title | Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions |
| title_full | Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions |
| title_fullStr | Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions |
| title_full_unstemmed | Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions |
| title_short | Selective C-N σ Bond Cleavage in Azetidinyl Amides under Transition Metal-Free Conditions |
| title_sort | selective c n σ bond cleavage in azetidinyl amides under transition metal free conditions |
| topic | amides C-N σ bond cleavage sodium crown ether |
| url | https://www.mdpi.com/1420-3049/24/3/459 |
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