Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters
Abstract C–C bond cleavage and recombination provide an efficient strategy for the modification and reconstruction of molecule structures. Herein, we present a method for achieving amidation of aryl C(sp2)–H bond through the cleavage and recombination of C–C triple bond with the involvement of nitro...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2025-01-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-025-56370-3 |
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| author | Zi-Ying Wang Shoujun Wang Nan-Nan Dai Yao Xiao Yu Zhou Wen-Chan Tian Dongru Sun Qiang Li Yong Wang Wen-Ting Wei |
| author_facet | Zi-Ying Wang Shoujun Wang Nan-Nan Dai Yao Xiao Yu Zhou Wen-Chan Tian Dongru Sun Qiang Li Yong Wang Wen-Ting Wei |
| author_sort | Zi-Ying Wang |
| collection | DOAJ |
| description | Abstract C–C bond cleavage and recombination provide an efficient strategy for the modification and reconstruction of molecule structures. Herein, we present a method for achieving amidation of aryl C(sp2)–H bond through the cleavage and recombination of C–C triple bond with the involvement of nitrous acid esters. This method marks the instance of precise and controlled stepwise cleavage of C–C triple bond, offering a fresh perspective for the cleavage of such bonds. Nitrous acid ester serves as both a radical source and a hydrogen atom transfer (HAT) reagent to functionalize and utilize the two carbon atoms of the C–C triple bond. The alkoxy radical captures the hydrogen atom from the aryl C(sp2)–H bond or N-hydroxyl to induce the 1,3-oxygen radical migration, which is crucial for the subsequent cleavage of the C–C bond. |
| format | Article |
| id | doaj-art-71bd3b313b5144978088d6ea48a20a79 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-71bd3b313b5144978088d6ea48a20a792025-01-26T12:40:59ZengNature PortfolioNature Communications2041-17232025-01-011611810.1038/s41467-025-56370-3Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid estersZi-Ying Wang0Shoujun Wang1Nan-Nan Dai2Yao Xiao3Yu Zhou4Wen-Chan Tian5Dongru Sun6Qiang Li7Yong Wang8Wen-Ting Wei9School of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversityShandong Provincial Key Laboratory of Chemical Energy Storage and Novel Cell Technology, School of Chemistry and Chemical Engineering, Liaocheng UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversitySchool of Materials Science and Chemical Engineering, Institute of Drug Discovery Technology, Institute of Mass Spectrometry, Zhejiang Engineering Research Center of Advanced Mass Spectrometry and Clinical Application, Ningbo UniversityAbstract C–C bond cleavage and recombination provide an efficient strategy for the modification and reconstruction of molecule structures. Herein, we present a method for achieving amidation of aryl C(sp2)–H bond through the cleavage and recombination of C–C triple bond with the involvement of nitrous acid esters. This method marks the instance of precise and controlled stepwise cleavage of C–C triple bond, offering a fresh perspective for the cleavage of such bonds. Nitrous acid ester serves as both a radical source and a hydrogen atom transfer (HAT) reagent to functionalize and utilize the two carbon atoms of the C–C triple bond. The alkoxy radical captures the hydrogen atom from the aryl C(sp2)–H bond or N-hydroxyl to induce the 1,3-oxygen radical migration, which is crucial for the subsequent cleavage of the C–C bond.https://doi.org/10.1038/s41467-025-56370-3 |
| spellingShingle | Zi-Ying Wang Shoujun Wang Nan-Nan Dai Yao Xiao Yu Zhou Wen-Chan Tian Dongru Sun Qiang Li Yong Wang Wen-Ting Wei Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters Nature Communications |
| title | Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| title_full | Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| title_fullStr | Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| title_full_unstemmed | Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| title_short | Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| title_sort | carbon carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters |
| url | https://doi.org/10.1038/s41467-025-56370-3 |
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