• 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

通过铑催化的芳基C-H活化实现苄基硫醚的可控单烯基化/双烯基化反应

Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl C-H Activation.

作者信息

Zhang Xi-Sha, Zhu Qi-Lei, Zhang Yun-Fei, Li Yan-Bang, Shi Zhang-Jie

机构信息

Beijing National Laboratory of Molecular Sciences (BNLMS) and Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering and Green Chemistry Center, Peking University, Beijing 100871 (P.R. China).

出版信息

Chemistry. 2013 Sep 2;19(36):11898-903. doi: 10.1002/chem.201300829. Epub 2013 Aug 16.

DOI:10.1002/chem.201300829
PMID:23955553
Abstract

Under solvent control: Benzyl thioethers were alkenylated in excellent yields with broad substrate scope and the selectivity (mono- vs. disubstituted product) was controlled by the solvent and ratio of reactants. Sequential alkenylation with two different alkenes was also carried out in a one-pot process. In addition, the thioether directing group was removed in a one-pot process with simultaneous hydrogenation of the double bond to give the toluene derivatives.

摘要

在溶剂控制下

苄基硫醚能以优异的产率进行烯基化反应，底物范围广泛，且（单取代与双取代产物的）选择性可通过溶剂和反应物比例来控制。还能在一锅法中用两种不同的烯烃进行连续烯基化反应。此外，硫醚导向基团可在一锅法中被去除，同时双键氢化得到甲苯衍生物。

相似文献

1
Controllable Mono-/Dialkenylation of Benzyl Thioethers through Rh-Catalyzed Aryl C-H Activation.通过铑催化的芳基C-H活化实现苄基硫醚的可控单烯基化/双烯基化反应
Chemistry. 2013 Sep 2;19(36):11898-903. doi: 10.1002/chem.201300829. Epub 2013 Aug 16.
2
Synthesis of dibenzo[c,e]oxepin-5(7H)-ones from benzyl thioethers and carboxylic acids: rhodium-catalyzed double C-H activation controlled by different directing groups.二苯并[c,e]氧杂环庚烯-5(7H)-酮的合成：由苄基硫醚和羧酸出发，通过不同导向基团控制的铑催化双 C-H 活化。
Angew Chem Int Ed Engl. 2015 Apr 27;54(18):5478-82. doi: 10.1002/anie.201500486. Epub 2015 Mar 10.
3
Rhodium(III)-Catalyzed C-H Bond Functionalization of 2-Pyridones with Alkynes: Switchable Alkenylation, Alkenylation/Directing Group Migration and Rollover Annulation.铑(III)催化 2-吡啶酮与炔烃的 C-H 键功能化反应：可切换的烯基化、烯基化/导向基团迁移和滚环式环化。
Chemistry. 2021 Jun 16;27(34):8811-8821. doi: 10.1002/chem.202101074. Epub 2021 May 7.
4
Rhodium-catalyzed directed sulfenylation of arene C-H bonds.铑催化的芳烃 C-H 键导向硫醚化反应。
Chemistry. 2014 Jan 7;20(2):416-20. doi: 10.1002/chem.201303730. Epub 2013 Nov 28.
5
Palladium-catalyzed C-H alkenylation of arenes using thioethers as directing groups.钯催化的芳基 C-H 烯基化反应，使用硫醚作为导向基团。
Org Lett. 2012 Apr 20;14(8):2164-7. doi: 10.1021/ol3006997. Epub 2012 Apr 6.
6
A one-pot synthesis of (E)-disubstituted alkenes by a bimetallic [Rh-Pd]-catalyzed hydrosilylation/hiyama cross-coupling sequence.通过双金属[Rh-Pd]催化的硅氢化/Hiyama交叉偶联序列一锅法合成(E)-二取代烯烃。
Chemistry. 2007;13(32):8971-8. doi: 10.1002/chem.200700811.
7
Rhodium(III)-Catalyzed C-H Alkenylation/Directing Group Migration for the Regio- and Stereoselective Synthesis of Tetrasubstituted Alkenes.铑(III)催化的 C-H 烯丙基化/导向基团迁移反应用于区域和立体选择性合成四取代烯烃。
Org Lett. 2020 Dec 4;22(23):9163-9168. doi: 10.1021/acs.orglett.0c03077. Epub 2020 Nov 16.
8
Rhodium(III)-catalyzed oxidative alkenylation of 1,3-dithiane-protected arenecarbaldehydes via regioselective C-H bond cleavage.铑(III)催化通过区域选择性 C-H 键断裂的 1,3-二硫杂环戊烷保护的芳基醛的氧化烯丙基化反应。
Org Lett. 2015 Feb 6;17(3):704-7. doi: 10.1021/ol503722r. Epub 2015 Jan 16.
9
Rhodium(II)-catalyzed nondirected oxidative alkenylation of arenes: arene loading at one equivalent.铑(II)催化的芳烃无导向氧化烯基化反应：芳烃以当量 1 加载。
Angew Chem Int Ed Engl. 2014 Mar 3;53(10):2683-6. doi: 10.1002/anie.201310539. Epub 2014 Jan 30.
10
Rh-catalyzed C-C cleavage of benzyl/allylic alcohols to produce benzyl/allylic amines or other alcohols by nucleophilic addition of intermediate rhodacycles to aldehydes and imines.铑催化的苄基/烯丙醇的 C-C 裂解，通过中间铑环对醛和亚胺的亲核加成，生成苄基/烯丙基胺或其他醇。
Chemistry. 2012 Dec 7;18(50):16214-25. doi: 10.1002/chem.201201867. Epub 2012 Oct 18.

引用本文的文献

1
Mechanistic study of enantioselective Pd-catalyzed C(sp)-H activation of thioethers involving two distinct stereomodels.涉及两种不同立体模型的对映选择性钯催化硫醚C(sp)-H活化的机理研究。
ACS Catal. 2021 Aug 6;11(15):9738-9753. doi: 10.1021/acscatal.1c02808. Epub 2021 Jul 19.
2
Ir(iii)-catalyzed thioether directed arene C-H alkenylation.铱（III）催化的硫醚导向芳烃C-H烯基化反应。
RSC Adv. 2019 Sep 24;9(52):30134-30138. doi: 10.1039/c9ra06811b. eCollection 2019 Sep 23.
3
Thioether-enabled palladium-catalyzed atroposelective C-H olefination for N-C and C-C axial chirality.
用于构建N-C和C-C轴手性的硫醚导向钯催化的对映选择性C-H烯基化反应
Chem Sci. 2022 Mar 10;13(14):4088-4094. doi: 10.1039/d2sc00748g. eCollection 2022 Apr 6.
4
Transition-metal-catalyzed remote C-H functionalization of thioethers.过渡金属催化的硫醚远程C-H官能团化反应
RSC Adv. 2022 Apr 7;12(17):10835-10845. doi: 10.1039/d2ra01268e. eCollection 2022 Mar 31.
5
Base-Assisted C-H Bond Cleavage in Cross-Coupling: Recent Insights into Mechanism, Speciation, and Cooperativity.交叉偶联反应中碱辅助的C-H键裂解：关于机理、物种形成和协同作用的最新见解
Isr J Chem. 2020 Mar;60(3-4):230-258. doi: 10.1002/ijch.201900095. Epub 2019 Dec 13.
6
Rhodium catalyzed template-assisted distal -C-H olefination.铑催化的模板辅助远程C-H烯基化反应。
Chem Sci. 2019 Jun 21;10(31):7426-7432. doi: 10.1039/c9sc01824g. eCollection 2019 Aug 21.
7
Substrate-Selective C-H Functionalization for the Preparation of Organosulfur Compounds from Crude Oil-Derived Components.基于原油衍生组分制备有机硫化合物的底物选择性C-H官能化反应
ACS Omega. 2017 Apr 11;2(4):1419-1423. doi: 10.1021/acsomega.7b00137. eCollection 2017 Apr 30.
8
Dithiane-directed Rh(iii)-catalyzed amidation of unactivated C(sp)-H bonds.二硫烷导向的铑（III）催化未活化C（sp）-H键的酰胺化反应
Chem Sci. 2019 Feb 18;10(13):3733-3737. doi: 10.1039/c8sc05225e. eCollection 2019 Apr 7.
9
A comprehensive overview of directing groups applied in metal-catalysed C-H functionalisation chemistry.指导基团在金属催化 C-H 官能化化学中的应用综述。
Chem Soc Rev. 2018 Aug 28;47(17):6603-6743. doi: 10.1039/c8cs00201k.
10
Rh(iii)-catalyzed C-H olefination of -pentafluoroaryl benzamides using air as the sole oxidant.使用空气作为唯一氧化剂，铑（III）催化的对五氟芳基苯甲酰胺的C-H烯基化反应。
Chem Sci. 2015 Mar 1;6(3):1923-1927. doi: 10.1039/c4sc03350g. Epub 2015 Jan 8.