• 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

在材料的苯并噻吩基组分的便捷合成中,亚砜导向的无金属交叉偶联反应。

Sulfoxide-directed metal-free cross-couplings in the expedient synthesis of benzothiophene-based components of materials.

作者信息

Eberhart Andrew J, Shrives Harry, Zhang Yuntong, Carrër Amandine, Parry Adam V S, Tate Daniel J, Turner Michael L, Procter David J

机构信息

School of Chemistry , University of Manchester , Oxford Rd , Manchester , M13 9PL , UK . Email:

出版信息

Chem Sci. 2016 Feb 1;7(2):1281-1285. doi: 10.1039/c5sc03823e. Epub 2015 Nov 9.

DOI:10.1039/c5sc03823e
PMID:29910885
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5975836/
Abstract

A metal-free approach combining sulfoxide-directed metal-free C-H cross-couplings with tuneable electrophile-mediated heterocyclizations and carbocyclative dimerizations, allows expedient access to benzothiophene-based systems that are components of important materials or are proven organic materials in their own right. As benzothiophene-based materials are typically prepared using Pd-catalyzed cross-coupling processes, our approach allows potential issues of metal cost and supply, and metal-contamination of products, to be avoided.

摘要

一种无金属方法,将亚砜导向的无金属C-H交叉偶联与可调亲电试剂介导的杂环化和碳环化二聚反应相结合,能够便捷地合成基于苯并噻吩的体系,这些体系是重要材料的组成部分,或者本身就是经过验证的有机材料。由于基于苯并噻吩的材料通常使用钯催化的交叉偶联过程制备,我们的方法可以避免金属成本和供应以及产品金属污染等潜在问题。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/c55396586264/c5sc03823e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/68e0b178623e/c5sc03823e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/22e87cae5430/c5sc03823e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/02036256cc48/c5sc03823e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/ab1ea0a28dfc/c5sc03823e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/39513bdc65b8/c5sc03823e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/ec8607e87641/c5sc03823e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/09d897e97d8c/c5sc03823e-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/c55396586264/c5sc03823e-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/68e0b178623e/c5sc03823e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/22e87cae5430/c5sc03823e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/02036256cc48/c5sc03823e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/ab1ea0a28dfc/c5sc03823e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/39513bdc65b8/c5sc03823e-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/ec8607e87641/c5sc03823e-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/09d897e97d8c/c5sc03823e-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3c67/5975836/c55396586264/c5sc03823e-s7.jpg

相似文献

1
Sulfoxide-directed metal-free cross-couplings in the expedient synthesis of benzothiophene-based components of materials.在材料的苯并噻吩基组分的便捷合成中,亚砜导向的无金属交叉偶联反应。
Chem Sci. 2016 Feb 1;7(2):1281-1285. doi: 10.1039/c5sc03823e. Epub 2015 Nov 9.
2
Sulfoxide-Directed or 3d-Metal Catalyzed C-H Activation and Hypervalent Iodines as Tools for Atroposelective Synthesis.亚砜导向或3d金属催化的C-H活化以及高价碘作为阻转选择性合成的工具
Acc Chem Res. 2023 Feb 7;56(3):189-202. doi: 10.1021/acs.accounts.2c00573. Epub 2023 Jan 27.
3
Metal-Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S-Oxides.无金属条件下 C4 位芳基化的苯并噻吩:苯并噻吩 S-氧化物的活化策略
Angew Chem Int Ed Engl. 2023 Jul 17;62(29):e202302418. doi: 10.1002/anie.202302418. Epub 2023 May 24.
4
The Interrupted Pummerer Reaction in a Sulfoxide-Catalyzed Oxidative Coupling of 2-Naphthols.亚砜催化 2-萘酚氧化偶联反应中的中断 Pummerer 反应。
Angew Chem Int Ed Engl. 2019 Jun 3;58(23):7813-7817. doi: 10.1002/anie.201903492. Epub 2019 May 6.
5
Cobalt-Catalyzed Cross-Couplings between Alkyl Halides and Grignard Reagents.钴催化的卤代烷烃与格氏试剂的交叉偶联反应。
Acc Chem Res. 2020 Jul 21;53(7):1351-1363. doi: 10.1021/acs.accounts.0c00238. Epub 2020 Jul 10.
6
Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated C(sp)-H activation.通过介导的C(sp)-H活化实现的钯催化交叉亲电偶联/C-H烷基化反应
Chem Sci. 2021 May 19;12(24):8531-8536. doi: 10.1039/d1sc01731d.
7
Well-Defined Palladium(II)-NHC Precatalysts for Cross-Coupling Reactions of Amides and Esters by Selective N-C/O-C Cleavage.通过选择性N-C/O-C裂解实现酰胺和酯交叉偶联反应的明确钯(II)-NHC预催化剂
Acc Chem Res. 2018 Oct 16;51(10):2589-2599. doi: 10.1021/acs.accounts.8b00410. Epub 2018 Sep 21.
8
Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings.通过析氢交叉偶联实现低活性键的光催化活化及其功能化
Acc Chem Res. 2018 Oct 16;51(10):2512-2523. doi: 10.1021/acs.accounts.8b00267. Epub 2018 Oct 3.
9
Transition-Metal-Catalyzed Cross-Couplings through Carbene Migratory Insertion.过渡金属催化的通过卡宾迁移插入的交叉偶联反应。
Chem Rev. 2017 Dec 13;117(23):13810-13889. doi: 10.1021/acs.chemrev.7b00382. Epub 2017 Nov 1.
10
Chiral Benzothiophene Synthesis via Enantiospecific Coupling of Benzothiophene S-Oxides with Boronic Esters.手性苯并噻吩的对映选择性合成通过苯并噻吩 S-氧化物与硼酸酯的偶联反应。
Angew Chem Int Ed Engl. 2021 Nov 22;60(48):25313-25317. doi: 10.1002/anie.202112180. Epub 2021 Nov 2.

引用本文的文献

1
Transition Metal-Free Formal C─H/C─H Coupling of Arylacetamides and Sulfoxides: An Interrupted Pummerer/[2,3]-sigmatropic Rearrangement Sequence.芳基乙酰胺与亚砜的无过渡金属形式的C─H/C─H偶联:一种中断的普默勒尔/[2,3]-σ迁移重排序列
Angew Chem Int Ed Engl. 2025 Sep 8;64(37):e202511703. doi: 10.1002/anie.202511703. Epub 2025 Jul 29.
2
An Iron-Catalyzed Sustainable Functional Group Transfer Strategy for In-Water Transformation of Organic Sulfides to Sulfoxides by a Hydroxylamine-Derived Oxidant.一种铁催化的可持续官能团转移策略:通过羟胺衍生的氧化剂在水中将有机硫化物转化为亚砜
ChemSusChem. 2025 Jun 17;18(12):e202500032. doi: 10.1002/cssc.202500032. Epub 2025 Apr 11.
3

本文引用的文献

1
Naphthodithiophene-Based Donor-Acceptor Polymers: Versatile Semiconductors for OFETs and OPVs.基于萘并二噻吩的给体-受体聚合物:用于有机场效应晶体管和有机光伏电池的多功能半导体
ACS Macro Lett. 2012 Apr 17;1(4):437-440. doi: 10.1021/mz300065t. Epub 2012 Mar 13.
2
Sulfoxide-Directed Metal-Free ortho-Propargylation of Aromatics and Heteroaromatics.砜氧化物导向的芳烃和杂芳烃无金属邻炔丙基化反应
Chemistry. 2015 May 11;21(20):7428-34. doi: 10.1002/chem.201406424. Epub 2015 Mar 6.
3
Naphthodithiophenes: emerging building blocks for organic electronics.
Metal-Free Arylation of Benzothiophenes at C4 by Activation as their Benzothiophene S-Oxides.
无金属条件下 C4 位芳基化的苯并噻吩:苯并噻吩 S-氧化物的活化策略
Angew Chem Int Ed Engl. 2023 Jul 17;62(29):e202302418. doi: 10.1002/anie.202302418. Epub 2023 May 24.
4
Dearomative di- and trifunctionalization of aryl sulfoxides via [5,5]-rearrangement.芳基砜的[5,5]-重排去芳构化双和三官能化。
Nat Commun. 2022 Aug 11;13(1):4719. doi: 10.1038/s41467-022-32426-6.
5
Sulfonium-aided coupling of aromatic rings via sigmatropic rearrangement.通过[重排反应]实现含硫鎓盐的芳环偶联反应。
Proc Jpn Acad Ser B Phys Biol Sci. 2022;98(4):190-205. doi: 10.2183/pjab.98.012.
6
Modular synthesis of unsymmetrical [1]benzothieno[3,2-][1]benzothiophene molecular semiconductors for organic transistors.用于有机晶体管的不对称[1]苯并噻吩并[3,2-][1]苯并噻吩分子半导体的模块化合成
Chem Sci. 2021 Nov 29;13(2):421-429. doi: 10.1039/d1sc05070b. eCollection 2022 Jan 5.
7
Dearomatization of aryl sulfoxides: a switch between mono- and dual-difluoroalkylation.芳基亚砜的脱芳构化:单氟烷基化与双氟烷基化之间的转换
Chem Sci. 2020 Feb 25;11(11):3048-3053. doi: 10.1039/d0sc00244e.
8
One-step synthesis of benzo[]thiophenes by aryne reaction with alkynyl sulfides.通过芳炔与炔基硫化物反应一步合成苯并[]噻吩。
Chem Sci. 2020 Sep 1;11(35):9691-9696. doi: 10.1039/d0sc04450d.
9
Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.硫(IV)的成键和断键反应:亚砜、锍盐、叶立德和亚磺酸盐。
Chem Rev. 2019 Jul 24;119(14):8701-8780. doi: 10.1021/acs.chemrev.9b00111. Epub 2019 Jun 25.
10
Regioselective synthesis of C3 alkylated and arylated benzothiophenes.C3 位烷基化和芳基化苯并噻吩的区域选择性合成。
Nat Commun. 2017 Mar 20;8:14801. doi: 10.1038/ncomms14801.
萘并二噻吩:有机电子学中新兴的结构单元。
Chem Rec. 2015 Feb;15(1):175-88. doi: 10.1002/tcr.201402051. Epub 2014 Oct 23.
4
Synthesis of extended π-systems through C-H activation.通过 C-H 活化合成扩展的π-体系。
Angew Chem Int Ed Engl. 2015 Jan 2;54(1):66-81. doi: 10.1002/anie.201403729. Epub 2014 Sep 26.
5
Palladium-catalyzed amination of aryl sulfides with anilines.钯催化的芳基硫醚与苯胺的胺化反应。
Angew Chem Int Ed Engl. 2014 Aug 25;53(35):9329-33. doi: 10.1002/anie.201404355. Epub 2014 Jul 7.
6
Practical, modular, and general synthesis of benzofurans through extended Pummerer annulation/cross-coupling strategy.通过扩展的 Pummerer 环化/交叉偶联策略实现苯并呋喃的实用、模块化和通用合成。
Angew Chem Int Ed Engl. 2014 Jul 14;53(29):7510-3. doi: 10.1002/anie.201403288. Epub 2014 Jun 12.
7
Metal impurities cause false positives in high-throughput screening campaigns.金属杂质会在高通量筛选活动中导致假阳性结果。
ACS Med Chem Lett. 2012 Dec 12;4(2):197-200. doi: 10.1021/ml3003296. eCollection 2013 Feb 14.
8
High-performance solution-processable N-shaped organic semiconducting materials with stabilized crystal phase.具有稳定晶体相的高性能溶液处理 N 型有机半导体材料。
Adv Mater. 2014 Jul 9;26(26):4546-51. doi: 10.1002/adma.201400289. Epub 2014 May 8.
9
Organic semiconductors based on [1]benzothieno[3,2-b][1]benzothiophene substructure.基于[1]苯并噻吩并[3,2-b][1]苯并噻吩结构的有机半导体。
Acc Chem Res. 2014 May 20;47(5):1493-502. doi: 10.1021/ar400282g. Epub 2014 May 1.
10
Chemoselective intermolecular α-arylation of amides.酰胺的化学选择性分子间 α-芳基化反应。
Angew Chem Int Ed Engl. 2014 May 19;53(21):5462-6. doi: 10.1002/anie.201402229. Epub 2014 Apr 16.