Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling
{"title":"电化学使环胺的去饱和β-C(sp3)-H磺化和膦化","authors":"Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling","doi":"10.1016/j.gresc.2023.11.008","DOIUrl":null,"url":null,"abstract":"<div><div>Herein, we reported an efficient and straightforward method to realize desaturated <em>β</em>-C(sp<sup>3</sup>)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP<sub>2</sub>Fe 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.</div></div>","PeriodicalId":12794,"journal":{"name":"Green Synthesis and Catalysis","volume":"5 4","pages":"Pages 297-302"},"PeriodicalIF":0.0000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemical enabled desaturated β-C(sp3)-H sulfonylation and phosphonylation of cyclic amines\",\"authors\":\"Tao Liu , Jie Lin , Fangjun Xia , Zhenhui Xu , Xuying Xia , Wei Qian , Weihui Zhong , Dingguo Song , Fei Ling\",\"doi\":\"10.1016/j.gresc.2023.11.008\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Herein, we reported an efficient and straightforward method to realize desaturated <em>β</em>-C(sp<sup>3</sup>)-H sulfonylation and phosphonylation of cyclic amines driven by electrochemistry using catalytic amounts of CP<sub>2</sub>Fe 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.</div></div>\",\"PeriodicalId\":12794,\"journal\":{\"name\":\"Green Synthesis and Catalysis\",\"volume\":\"5 4\",\"pages\":\"Pages 297-302\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-11-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Green Synthesis and Catalysis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666554923001023\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Green Synthesis and Catalysis","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666554923001023","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
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 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.