Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines
Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided th...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2024-11-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554923001023 |
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| author | Tao Liu Jie Lin Fangjun Xia Zhenhui Xu Xuying Xia Wei Qian Weihui Zhong Dingguo Song Fei Ling |
| author_facet | Tao Liu Jie Lin Fangjun Xia Zhenhui Xu Xuying Xia Wei Qian Weihui Zhong Dingguo Song Fei Ling |
| author_sort | Tao Liu |
| collection | DOAJ |
| description | Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products. |
| format | Article |
| id | doaj-art-ce07f84bbdc8409286a59d2f6e61ed0d |
| institution | Kabale University |
| issn | 2666-5549 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj-art-ce07f84bbdc8409286a59d2f6e61ed0d2024-11-30T07:14:17ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492024-11-0154297302Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic aminesTao Liu0Jie Lin1Fangjun Xia2Zhenhui Xu3Xuying Xia4Wei Qian5Weihui Zhong6Dingguo Song7Fei Ling8College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China; Chengda Pharmaceuticals Co., Ltd., Jiashan 314100, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, ChinaCollege of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China; Corresponding author. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China.College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China; Zhejiang Hisoar Pharmaceutical Co., Ltd., Taizhou 318000, China; Corresponding author. College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China.Herein, we reported an efficient and straightforward method to realize desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP2Fe as the redox mediator. This protocol which had good functional group compatibility, provided the desired enaminyl sulfone and enaminyl phosphine oxide products with high chemo- and regio-selectivity under mild conditions. Several mechanistic studies have suggested that cyclic amines underwent multiple single-electron oxidation and deprotonation processes, followed by a capture step involving either a sulfonyl radical or a phosphonyl radical, ultimately leading to the desired products.http://www.sciencedirect.com/science/article/pii/S2666554923001023ElectrocatalysisCyclic amineβ-FunctionalizationSulfonylationPhosphonylation |
| spellingShingle | Tao Liu Jie Lin Fangjun Xia Zhenhui Xu Xuying Xia Wei Qian Weihui Zhong Dingguo Song Fei Ling Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines Green Synthesis and Catalysis Electrocatalysis Cyclic amine β-Functionalization Sulfonylation Phosphonylation |
| title | Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines |
| title_full | Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines |
| title_fullStr | Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines |
| title_full_unstemmed | Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines |
| title_short | Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines |
| title_sort | electrochemical enabled desaturated β c sp3 h sulfonylation and phosphonylation of cyclic amines |
| topic | Electrocatalysis Cyclic amine β-Functionalization Sulfonylation Phosphonylation |
| url | http://www.sciencedirect.com/science/article/pii/S2666554923001023 |
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