Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles
Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp<sup>3</sup>)–H/N–H c...
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| Format: | Article |
| Language: | English |
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2024-12-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/1/4 |
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| author | Guoping Li Bing Yan Liangliang Wu Yabo Li Xinqi Hao Ming Gong Yangjie Wu |
| author_facet | Guoping Li Bing Yan Liangliang Wu Yabo Li Xinqi Hao Ming Gong Yangjie Wu |
| author_sort | Guoping Li |
| collection | DOAJ |
| description | Isochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp<sup>3</sup>)–H/N–H cross-coupling reactions between isochromans and azoles, yielding products in moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants and can be performed at room temperature under air. Control experiments and cyclic voltammetry showed that the reaction may proceed through both radical coupling and nucleophilic addition processes. |
| format | Article |
| id | doaj-art-e937f799bca64f2ebbb4a745b833abc7 |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-e937f799bca64f2ebbb4a745b833abc72025-01-10T13:18:33ZengMDPI AGMolecules1420-30492024-12-01301410.3390/molecules30010004Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and AzolesGuoping Li0Bing Yan1Liangliang Wu2Yabo Li3Xinqi Hao4Ming Gong5Yangjie Wu6College of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaCollege of Chemistry, Henan Key Laboratory of Chemical Biology and Organic Chemistry, Key Laboratory of Applied Chemistry of Henan Universities, Zhengzhou University, Zhengzhou 450052, ChinaIsochroman and azole moieties are both present in a wide variety of biologically active molecules. Their efficient combination under mild reaction conditions is beneficial for obtaining small-molecule drug candidates. In this paper, we describe electrochemical α-C(sp<sup>3</sup>)–H/N–H cross-coupling reactions between isochromans and azoles, yielding products in moderate to excellent yields. This protocol does not require any catalysts or exogenous oxidants and can be performed at room temperature under air. Control experiments and cyclic voltammetry showed that the reaction may proceed through both radical coupling and nucleophilic addition processes.https://www.mdpi.com/1420-3049/30/1/4electro-oxidationcross-couplingisochromanazoleC–N bond formation |
| spellingShingle | Guoping Li Bing Yan Liangliang Wu Yabo Li Xinqi Hao Ming Gong Yangjie Wu Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles Molecules electro-oxidation cross-coupling isochroman azole C–N bond formation |
| title | Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles |
| title_full | Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles |
| title_fullStr | Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles |
| title_full_unstemmed | Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles |
| title_short | Electrochemical α-C(sp<sup>3</sup>)–H/N–H Cross-Coupling of Isochromans and Azoles |
| title_sort | electrochemical α c sp sup 3 sup h n h cross coupling of isochromans and azoles |
| topic | electro-oxidation cross-coupling isochroman azole C–N bond formation |
| url | https://www.mdpi.com/1420-3049/30/1/4 |
| work_keys_str_mv | AT guopingli electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT bingyan electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT liangliangwu electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT yaboli electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT xinqihao electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT minggong electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles AT yangjiewu electrochemicalacspsup3suphnhcrosscouplingofisochromansandazoles |