• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利:CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法,用中文像聊天一样搜索,搜遍4000万医学文献。AI智能推荐,让科研检索更轻松。

立即免费搜索

文件翻译

保留排版,准确专业,支持PDF/Word/PPT等文件格式,支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述,25分钟生成高质量综述,智能提取关键信息,辅助科研写作。

立即免费体验

光氧化还原催化的烯烃分子间自由基芳基硫氰化/芳基硒氰化反应:合成芳基取代的烷基硫氰酸酯/烷基硒氰酸酯

Photoredox-Catalyzed Intermolecular Radical Arylthiocyanation/Arylselenocyanation of Alkenes: Access to Aryl-Substituted Alkylthiocyanates/Alkylselenocyanates.

作者信息

Hoque Injamam Ul, Chowdhury Soumyadeep Roy, Maity Soumitra

机构信息

Department of Applied Chemistry , Indian Institute of Technology (ISM) Dhanbad , JH 826004 , India.

出版信息

J Org Chem. 2019 Mar 15;84(6):3025-3035. doi: 10.1021/acs.joc.8b03155. Epub 2019 Jan 23.

DOI:10.1021/acs.joc.8b03155
PMID:30665295
Abstract

An efficient and highly selective approach for intermolecular arylthiocyanation/arylselenocyanation of alkenes has been reported under mild conditions. Using diazonium salts as the arylating agent and ammonium thiocyanate as the thiocyanate source, chemoselective difunctionalization of alkenes has been done under irradiation of visible light. Both styrenes and acrylates work well to deliver various aryl-substituted alkylthiocyanates in good to excellent yields. In addition, hitherto unknown β-aryl alkylselenocyanates were also synthesized using the developed protocol with potassium selenocyanate.

摘要

据报道,在温和条件下已开发出一种高效且高选择性的方法用于烯烃的分子间芳基硫氰化/芳基硒氰化反应。以重氮盐作为芳基化试剂,硫氰酸铵作为硫氰酸源,在可见光照射下实现了烯烃的化学选择性双官能化反应。苯乙烯和丙烯酸酯均能顺利反应,以良好至优异的产率得到各种芳基取代的烷基硫氰酸酯。此外,使用所开发的方法,以硒氰酸钾为原料,还合成了迄今未知的β-芳基烷基硒氰酸酯。

相似文献

1
Photoredox-Catalyzed Intermolecular Radical Arylthiocyanation/Arylselenocyanation of Alkenes: Access to Aryl-Substituted Alkylthiocyanates/Alkylselenocyanates.光氧化还原催化的烯烃分子间自由基芳基硫氰化/芳基硒氰化反应:合成芳基取代的烷基硫氰酸酯/烷基硒氰酸酯
J Org Chem. 2019 Mar 15;84(6):3025-3035. doi: 10.1021/acs.joc.8b03155. Epub 2019 Jan 23.
2
Visible Light Mediated Photoredox Catalytic Arylation Reactions.可见光介导的光氧化还原催化芳基化反应。
Acc Chem Res. 2016 Aug 16;49(8):1566-77. doi: 10.1021/acs.accounts.6b00229. Epub 2016 Aug 2.
3
Ag/Pyridine Co-Mediated Oxidative Arylthiocyanation of Activated Alkenes.Ag/Pyridine 介导的活化烯烃的氧化芳基硫氰化反应。
Molecules. 2018 Oct 22;23(10):2727. doi: 10.3390/molecules23102727.
4
Generation of the SCF Radical by Photoredox Catalysis: Intra- and Intermolecular Carbotrifluoromethylthiolation of Alkenes.通过光氧化还原催化生成SCF自由基:烯烃的分子内和分子间三氟甲基硫基化反应
Chemistry. 2017 Mar 28;23(18):4282-4286. doi: 10.1002/chem.201700734. Epub 2017 Mar 13.
5
Arylthianthrenium Salts as the Aryl Sources: Visible Light/Copper Catalysis-Enabled Intermolecular Azidosulfonylation of Alkenes.芳基噻蒽鎓盐作为芳基源:可见光/铜催化的烯烃分子间叠氮磺酰化反应
Org Lett. 2024 Mar 8;26(9):1845-1850. doi: 10.1021/acs.orglett.4c00017. Epub 2024 Feb 26.
6
Visible-Light Photoredox-Catalyzed Hydroalkoxymethylation of Activated Alkenes Using α-Silyl Ethers as Alkoxymethyl Radical Equivalents.可见光光氧化还原催化的α-硅基醚作为烷氧基甲基自由基等价物的活化烯烃的氢烷氧基甲基化反应。
Org Lett. 2018 Oct 5;20(19):6239-6243. doi: 10.1021/acs.orglett.8b02721. Epub 2018 Sep 18.
7
Photosensitizer-Free Visible-Light-Mediated Gold-Catalyzed 1,2-Difunctionalization of Alkynes.无敏化剂可见光促进的炔烃的金催化 1,2-双官能化反应。
Angew Chem Int Ed Engl. 2016 Apr 4;55(15):4808-13. doi: 10.1002/anie.201511487. Epub 2016 Mar 11.
8
syn-Selective alkylarylation of terminal alkynes via the combination of photoredox and nickel catalysis.通过光氧化还原和镍催化的组合实现末端炔烃的 syn-选择性芳基烷基化反应。
Nat Commun. 2018 Oct 31;9(1):4543. doi: 10.1038/s41467-018-06904-9.
9
Photoredox Hydroxy-arylation of the Terminal Double Bond of -Substituted 3-Methyleneisoindolin-1-ones in Visible Light.可见光下 - 取代的3 - 亚甲基异吲哚啉 - 1 - 酮末端双键的光氧化还原羟基芳基化反应
J Org Chem. 2022 Sep 16;87(18):11939-11946. doi: 10.1021/acs.joc.2c00607. Epub 2022 Aug 30.
10
Intermolecular aminotrifluoromethylation of alkenes by visible-light-driven photoredox catalysis.可见光驱动光氧化还原催化的烯烃分子间氨基三氟甲基化反应。
Org Lett. 2013 May 3;15(9):2136-9. doi: 10.1021/ol4006272. Epub 2013 Apr 19.

引用本文的文献

1
Light-assisted functionalization of aryl radicals towards metal-free cross-coupling.芳基自由基的光辅助官能团化用于无金属交叉偶联反应
Nat Rev Chem. 2025 Jan;9(1):61-80. doi: 10.1038/s41570-024-00664-5. Epub 2024 Nov 15.
2
Photocascade chemoselective controlling of ambident thio(seleno)cyanates with alkenes via catalyst modulation.通过催化剂调控实现烯烃对硫(硒)氰酸酯的光级联化学选择性控制。
Nat Commun. 2024 Jul 9;15(1):5739. doi: 10.1038/s41467-024-49279-w.
3
Visible light mediated organocatalytic dehydrogenative aza-coupling of 1,3-diones using aryldiazonium salts.
可见光介导的芳基重氮盐与1,3 - 二酮的有机催化脱氢氮杂偶联反应
RSC Adv. 2023 Jan 20;13(5):3147-3154. doi: 10.1039/d2ra07807d. eCollection 2023 Jan 18.
4
Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation.光化学和电化学诱导硫氰化反应的最新进展:一种更绿色的含硫氰基化合物形成方法。
RSC Adv. 2022 Feb 22;12(10):6214-6233. doi: 10.1039/d1ra09060g. eCollection 2022 Feb 16.