• 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

铑(III)催化的通过 C-H 活化的钾乙烯三氟硼酸盐的互补区域选择性插入:4-三氟硼酸盐四氢异喹啉的制备和用途。

Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

机构信息

Roy and Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States.

出版信息

Org Lett. 2013 Apr 5;15(7):1528-31. doi: 10.1021/ol400307d. Epub 2013 Mar 15.

DOI:10.1021/ol400307d
PMID:23496033
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3663910/
Abstract

Potassium vinyltrifluoroborate was found to be an efficient partner with benzamide derivatives for Rh(III)-catalyzed annulations. 4-Trifluoroboratotetrahydroisoquinolones were generated under mild conditions, affording a regioisomerically complementary substitution pattern to other alkenes in related reactions. These new boron-containing building blocks were derivatized by N-arylations, retaining the boron substituent for further elaboration.

摘要

发现乙烯基三氟硼酸钾与苯甲酰胺衍生物是 Rh(III)催化环化反应的有效搭档。在温和条件下生成了 4-三氟硼酸盐四氢异喹啉酮,提供了与相关反应中其他烯烃不同的区域异构体互补取代模式。这些新的含硼砌块可通过 N-芳基化进行衍生化,保留硼取代基以进行进一步的修饰。

相似文献

1
Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.铑(III)催化的通过 C-H 活化的钾乙烯三氟硼酸盐的互补区域选择性插入:4-三氟硼酸盐四氢异喹啉的制备和用途。
Org Lett. 2013 Apr 5;15(7):1528-31. doi: 10.1021/ol400307d. Epub 2013 Mar 15.
2
Palladium-catalyzed allylic C-H fluorination.钯催化的烯丙基 C-H 氟化反应。
J Am Chem Soc. 2013 Sep 4;135(35):12990-3. doi: 10.1021/ja407223g. Epub 2013 Aug 20.
3
One-pot cascade synthesis of N-methoxyisoquinolinediones via Rh(III)-catalyzed carbenoid insertion C-H activation/cyclization.通过铑(III)催化的类卡宾插入C-H活化/环化一锅法串联合成N-甲氧基异喹啉二酮
Chem Commun (Camb). 2015 Jan 14;51(4):668-71. doi: 10.1039/c4cc08407a.
4
Rhodium(III)-catalyzed cyclization-olefination of N-acetoxyl ketoimine-alkynes.铑(III)催化的 N-乙酰氧基酮亚胺-炔烃的环化-烯烃化反应。
Org Lett. 2012 Jul 6;14(13):3400-3. doi: 10.1021/ol301371p. Epub 2012 Jun 12.
5
Synthesis of 1-aminoisoquinolines via Rh(III)-catalyzed oxidative coupling.通过 Rh(III)催化的氧化偶联反应合成 1-氨基异喹啉。
Org Lett. 2011 Sep 2;13(17):4636-9. doi: 10.1021/ol2018505. Epub 2011 Aug 3.
6
Rh(III)-catalyzed directed C-H olefination using an oxidizing directing group: mild, efficient, and versatile.铑(III)催化的使用氧化导向基团的导向 C-H 烯化反应:温和、高效、多功能。
J Am Chem Soc. 2011 Mar 2;133(8):2350-3. doi: 10.1021/ja109676d. Epub 2011 Jan 28.
7
Direct Regio- and Diastereoselective Synthesis of δ-Lactams from Acrylamides and Unactivated Alkenes Initiated by Rh -Catalyzed C-H Activation.铑催化 C-H 活化引发的丙烯酰胺与非活化烯烃的 δ-内酰胺的区域和立体选择性直接合成。
Angew Chem Int Ed Engl. 2020 Mar 16;59(12):4965-4969. doi: 10.1002/anie.201916332. Epub 2020 Feb 11.
8
Cp*Rh(III)-Catalyzed C-H Bond Difluorovinylation of Indoles with α,α-Difluorovinyl Tosylate.Cp*Rh(III)-催化的吲哚与α,α-二氟乙烯基对甲苯磺酸酯的 C-H 键双氟乙烯基化反应。
J Org Chem. 2019 Jun 7;84(11):7320-7330. doi: 10.1021/acs.joc.9b00957. Epub 2019 May 29.
9
Palladium(0)-catalyzed cross-coupling of potassium (Z)-2-chloroalk-1-enyl trifluoroborates: a chemo- and stereoselective access to (Z)-chloroolefins and trisubstituted alkenes.钯(0)催化的(Z)-2-氯代烯基三氟硼酸钾的交叉偶联反应:一种化学和立体选择性合成(Z)-氯代烯烃和三取代烯烃的方法。
Chemistry. 2009 Jun 2;15(23):5793-8. doi: 10.1002/chem.200900425.
10
Rh(III)-catalyzed regioselective synthesis of pyridines from alkenes and α,β-unsaturated oxime esters.铱(III)催化烯烃和α,β-不饱和肟酯的区域选择性合成吡啶。
J Am Chem Soc. 2013 Jan 9;135(1):66-9. doi: 10.1021/ja3104389. Epub 2012 Dec 18.

引用本文的文献

1
Three-component 1,2-carboamination of vinyl boronic esters amidyl radical induced 1,2-migration.乙烯基硼酸酯的三组分1,2-碳胺化反应:酰胺基自由基引发的1,2-迁移
Chem Sci. 2021 Nov 16;12(47):15765-15769. doi: 10.1039/d1sc05811h. eCollection 2021 Dec 8.
2
Regio- and Stereoselective Synthesis of the Core Structure of Hexahydrobenzo[]phenanthridine Alkaloids via Redox-Neutral Cp*Rh(III)-Catalyzed C-H/N-H Annulation of Cyclic Alkenes with Benzamides.通过氧化还原中性的Cp*Rh(III)催化环烯烃与苯甲酰胺的C-H/N-H环化反应实现六氢苯并[]菲啶生物碱核心结构的区域和立体选择性合成。
ACS Omega. 2020 Sep 10;5(37):24033-24044. doi: 10.1021/acsomega.0c03434. eCollection 2020 Sep 22.
3
Rh -Catalyzed C-H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones.Rh 催化的芳基羟肟酸的 C-H 活化反应用于异吲哚啉酮的合成。
Chemistry. 2020 Aug 21;26(47):10729-10734. doi: 10.1002/chem.202002384. Epub 2020 Jul 21.
4
From Pd(OAc) to Chiral Catalysts: The Discovery and Development of Bifunctional Mono-N-Protected Amino Acid Ligands for Diverse C-H Functionalization Reactions.从 Pd(OAc) 到手性催化剂:双功能单 N-保护氨基酸配体在各种 C-H 功能化反应中的发现和发展。
Acc Chem Res. 2020 Apr 21;53(4):833-851. doi: 10.1021/acs.accounts.9b00621. Epub 2020 Mar 31.
5
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.
6
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.
7
Expeditious Synthesis of Isoquinolones and Isocoumarins with a Vinyl Borane as an Acetylene Equivalent.以乙烯基硼烷作为乙炔等价物快速合成异喹啉酮和异香豆素
European J Org Chem. 2016 Aug;2016(24):4171-4175. doi: 10.1002/ejoc.201600575. Epub 2016 Jul 26.
8
Correlating Reactivity and Selectivity to Cyclopentadienyl Ligand Properties in Rh(III)-Catalyzed C-H Activation Reactions: An Experimental and Computational Study.在铑(III)催化的 C-H 活化反应中,关联反应活性和选择性与环戊二烯基配体性质:实验和计算研究。
J Am Chem Soc. 2017 Jan 25;139(3):1296-1310. doi: 10.1021/jacs.6b11670. Epub 2017 Jan 6.
9
Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction.通过氮杂-Heck反应合成仲不饱和内酰胺
J Am Chem Soc. 2016 Oct 26;138(42):13830-13833. doi: 10.1021/jacs.6b08932. Epub 2016 Oct 18.
10
Applications of Palladium-Catalyzed C-N Cross-Coupling Reactions.钯催化的碳-氮交叉偶联反应的应用
Chem Rev. 2016 Oct 12;116(19):12564-12649. doi: 10.1021/acs.chemrev.6b00512. Epub 2016 Sep 30.

本文引用的文献

1
Sequential Insertion of Alkynes, Alkenes, and CO into the Pd-C Bond of -Palladated Primary Phenethylamines: from η-Allyl Complexes and Enlarged Palladacycles to Functionalized Arylalkylamines.炔烃、烯烃和一氧化碳依次插入钯配位的伯苯乙胺的 Pd-C 键:从 η-烯丙基配合物和扩大的钯环到功能化芳基烷基胺
Organometallics. 2021 Feb 22;40(4):539-556. doi: 10.1021/acs.organomet.0c00787. Epub 2021 Jan 29.
2
Mild Rh(III)-catalyzed C-H activation and annulation with alkyne MIDA boronates: short, efficient synthesis of heterocyclic boronic acid derivatives.温和的 Rh(III)催化 C-H 活化和炔烃 MIDA 硼酸酯的环化反应:杂环硼酸衍生物的短、高效合成。
J Am Chem Soc. 2012 Dec 5;134(48):19592-5. doi: 10.1021/ja310153v. Epub 2012 Nov 20.
3
Chiral cyclopentadienyl ligands as stereocontrolling element in asymmetric C-H functionalization.手性环戊二烯基配体作为不对称 C-H 官能化反应中的立体控制因素。
Science. 2012 Oct 26;338(6106):504-6. doi: 10.1126/science.1226938.
4
Biotinylated Rh(III) complexes in engineered streptavidin for accelerated asymmetric C-H activation.用于加速不对称 C-H 活化的工程化链霉亲和素中的生物素化铑(III)配合物。
Science. 2012 Oct 26;338(6106):500-3. doi: 10.1126/science.1226132.
5
Rhodium(III)-catalyzed oxidative C-H coupling of N-methoxybenzamides with aryl boronic acids: one-pot synthesis of phenanthridinones.铑(III)催化的N-甲氧基苯甲酰胺与芳基硼酸的氧化C-H偶联反应:菲啶酮的一锅法合成
Angew Chem Int Ed Engl. 2012 Dec 3;51(49):12343-7. doi: 10.1002/anie.201206890. Epub 2012 Oct 26.
6
Rhodium(III)-catalyzed oxidative C-H functionalization of azomethine ylides.铑(III)催化的甲亚胺叶立德的氧化C-H官能团化反应
Angew Chem Int Ed Engl. 2012 Nov 19;51(47):11819-23. doi: 10.1002/anie.201207204. Epub 2012 Oct 19.
7
Rhodium(III) and hexabromobenzene-a catalyst system for the cross-dehydrogenative coupling of simple arenes and heterocycles with arenes bearing directing groups.三价铑和六溴苯-用于带有导向基团的芳基与简单芳环和杂环的交叉脱氢偶联的催化剂体系。
Angew Chem Int Ed Engl. 2012 Dec 21;51(52):13001-5. doi: 10.1002/anie.201205734. Epub 2012 Oct 19.
8
Rhodium-catalyzed oxidative annulation of sulfonylhydrazones with alkenes.铑催化的磺酰腙与烯烃的氧化环化反应。
Org Lett. 2012 Oct 19;14(20):5338-41. doi: 10.1021/ol302522n. Epub 2012 Oct 5.
9
Access to sultams by rhodium(III)-catalyzed directed C-H activation.通过铑(III)催化的导向 C-H 活化来获得磺胺。
Angew Chem Int Ed Engl. 2012 Oct 15;51(42):10610-4. doi: 10.1002/anie.201206191. Epub 2012 Sep 23.
10
Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: a synthetic route to diarylamines.铑催化的苯甲酰胺与芳基叠氮化物的直接 C-H 胺化反应:二芳基胺的合成途径。
Angew Chem Int Ed Engl. 2012 Sep 24;51(39):9904-8. doi: 10.1002/anie.201205723. Epub 2012 Aug 31.