Xin-Qian Liu, Jian-Hong Fan, Kewen Tang, Long-Jin Zhong, Yu Liu
{"title":"可见光诱导铜催化 1,7-二烯与锍盐的烷基化/外环化反应,以获得含硫多环化合物","authors":"Xin-Qian Liu, Jian-Hong Fan, Kewen Tang, Long-Jin Zhong, Yu Liu","doi":"10.1002/adsc.202400445","DOIUrl":null,"url":null,"abstract":"A direct visible-light-promoted radical-triggered tandem cyclization of 1,7-diene systems with cyclic sulfonium salts by using copper(I)-based complexes as photoredox catalyst is developed. With this approach, a variety of sulfur-containing polycyclic derivatives are prepared through alkylation/6-exo-trig cyclization/5-exo-trig cyclization of 1,7-diene systems under mild conditions. In addition, the photoinduced copper-catalyzed ring-opening of cyclic sulfonium salts provides the alkyl radical intermediates, which prefers addition to the Ph-linked C-C double bond rather than the electron-deficient vinyl in 1,7-dienes. Moreover, oxidation of the desire sulfur-containing polycyclic products provides a strategy for the preparation of remote nitrogen-fused polycyclic substituted sulfoxide or sulfone-containing derivatives.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":null,"pages":null},"PeriodicalIF":4.4000,"publicationDate":"2024-07-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Visible Light-Induced Copper-Catalyzed Alkylation/exo-Cyclization of 1,7-Dienes with Sulfonium Salts to Access Sulfur-Containing Polycyclic Compounds\",\"authors\":\"Xin-Qian Liu, Jian-Hong Fan, Kewen Tang, Long-Jin Zhong, Yu Liu\",\"doi\":\"10.1002/adsc.202400445\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"A direct visible-light-promoted radical-triggered tandem cyclization of 1,7-diene systems with cyclic sulfonium salts by using copper(I)-based complexes as photoredox catalyst is developed. With this approach, a variety of sulfur-containing polycyclic derivatives are prepared through alkylation/6-exo-trig cyclization/5-exo-trig cyclization of 1,7-diene systems under mild conditions. In addition, the photoinduced copper-catalyzed ring-opening of cyclic sulfonium salts provides the alkyl radical intermediates, which prefers addition to the Ph-linked C-C double bond rather than the electron-deficient vinyl in 1,7-dienes. Moreover, oxidation of the desire sulfur-containing polycyclic products provides a strategy for the preparation of remote nitrogen-fused polycyclic substituted sulfoxide or sulfone-containing derivatives.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-07-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202400445\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202400445","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
Visible Light-Induced Copper-Catalyzed Alkylation/exo-Cyclization of 1,7-Dienes with Sulfonium Salts to Access Sulfur-Containing Polycyclic Compounds
A direct visible-light-promoted radical-triggered tandem cyclization of 1,7-diene systems with cyclic sulfonium salts by using copper(I)-based complexes as photoredox catalyst is developed. With this approach, a variety of sulfur-containing polycyclic derivatives are prepared through alkylation/6-exo-trig cyclization/5-exo-trig cyclization of 1,7-diene systems under mild conditions. In addition, the photoinduced copper-catalyzed ring-opening of cyclic sulfonium salts provides the alkyl radical intermediates, which prefers addition to the Ph-linked C-C double bond rather than the electron-deficient vinyl in 1,7-dienes. Moreover, oxidation of the desire sulfur-containing polycyclic products provides a strategy for the preparation of remote nitrogen-fused polycyclic substituted sulfoxide or sulfone-containing derivatives.
期刊介绍:
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.