• 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

配体加速的 C(sp2)-H 键与芳基硼试剂的交叉偶联反应。

Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.

机构信息

Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

出版信息

J Am Chem Soc. 2011 Nov 16;133(45):18183-93. doi: 10.1021/ja203978r. Epub 2011 Oct 21.

DOI:10.1021/ja203978r
PMID:21913636
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3230269/
Abstract

A ligand-accelerated Pd(II)-catalyzed C(sp(2))-H/arylboron cross-coupling reaction of phenylacetic acid substrates is reported. Using Ac-Ile-OH as the ligand and Ag(2)CO(3) as the oxidant, a fast, high-yielding, operationally simple, and functional group-tolerant protocol has been developed for the cross-coupling of phenylacetic acid substrates with aryltrifluoroborates. This ligand scaffold has also been shown to improve catalysis using 1 atm O(2) as the sole reoxidant, which sheds light on the path forward in developing optimized ligands for aerobic C-H/arylboron cross-coupling.

摘要

报道了一种配体加速的 Pd(II)催化的 C(sp(2))-H/芳基硼酸交叉偶联反应,涉及苯乙酸底物。使用 Ac-Ile-OH 作为配体和 Ag(2)CO(3)作为氧化剂,开发了一种快速、高产、操作简单且官能团容忍的苯乙酸底物与芳基三氟硼酸盐交叉偶联的方法。该配体支架还被证明可以改善使用 1 atm O(2)作为唯一氧化剂的催化作用,为开发有氧 C-H/芳基硼酸交叉偶联的优化配体指明了方向。

相似文献

1
Ligand-accelerated cross-coupling of C(sp2)-H bonds with arylboron reagents.配体加速的 C(sp2)-H 键与芳基硼试剂的交叉偶联反应。
J Am Chem Soc. 2011 Nov 16;133(45):18183-93. doi: 10.1021/ja203978r. Epub 2011 Oct 21.
2
Versatile Pd(II)-catalyzed C-H activation/aryl-aryl coupling of benzoic and phenyl acetic acids.通用的钯(II)催化苯甲酸和苯乙酸的C-H活化/芳基-芳基偶联反应
J Am Chem Soc. 2008 Dec 31;130(52):17676-7. doi: 10.1021/ja806681z.
3
Pd-catalyzed deoxygenation of mandelate esters.钯催化扁桃酸酯的脱氧反应。
J Org Chem. 2009 Jan 2;74(1):445-7. doi: 10.1021/jo8021499.
4
Ligand-accelerated ortho-C-H alkylation of arylcarboxylic acids using alkyl boron reagents.使用烷基硼试剂加速芳基羧酸的邻位 C-H 烷基化反应。
J Am Chem Soc. 2013 Nov 20;135(46):17508-13. doi: 10.1021/ja409014v. Epub 2013 Nov 8.
5
Palladium-catalyzed direct C-2 arylation of indoles with potassium aryltrifluoroborate salts.钯催化吲哚与芳基三氟硼酸钾盐的直接C-2芳基化反应。
J Org Chem. 2008 Sep 19;73(18):7428-31. doi: 10.1021/jo801371w. Epub 2008 Aug 15.
6
Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(0) catalysis.钯(II)/钯(0)催化通过配体促进的 C(sp3)-H 键与芳基硼试剂的交叉偶联。
Nat Chem. 2014 Feb;6(2):146-50. doi: 10.1038/nchem.1836. Epub 2014 Jan 5.
7
Palladium(II)-catalyzed ortho-arylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates.钯(II)催化的使用钾芳基三氟硼酸盐的苄基膦酸单酯的邻位芳基化反应。
J Org Chem. 2013 Nov 15;78(22):11247-54. doi: 10.1021/jo401716p. Epub 2013 Nov 1.
8
Palladium-catalyzed trans- and cis-carboboration of alkynes tethered to chloroborane with organozirconium reagents: ligand-dependent complementary stereoselectivity.钯催化连接氯硼烷的炔烃与有机锆试剂的反式和顺式碳硼化反应:配体依赖性互补立体选择性
J Am Chem Soc. 2008 Mar 12;130(10):2918-9. doi: 10.1021/ja711160h. Epub 2008 Feb 16.
9
Accessing molecularly complex azaborines: palladium-catalyzed Suzuki-Miyaura cross-couplings of brominated 2,1-borazaronaphthalenes and potassium organotrifluoroborates.获取分子结构复杂的氮杂硼苯:钯催化溴代2,1-硼氮萘与有机三氟硼酸钾的铃木-宫浦交叉偶联反应
J Org Chem. 2014 Jul 18;79(14):6663-78. doi: 10.1021/jo5011894. Epub 2014 Jul 1.
10
Ir-catalyzed preparation of SF5-substituted potassium aryl trifluoroborates via C-H borylation and their application in the Suzuki-Miyaura reaction.铱催化通过 C-H 硼化反应制备 SF5 取代的芳基三氟硼酸钾盐及其在铃木-宫浦反应中的应用。
Org Lett. 2013 Oct 18;15(20):5147-9. doi: 10.1021/ol4025666. Epub 2013 Oct 3.

引用本文的文献

1
Divergent Kinetic/Thermodynamic Selectivity in Palladium(II)-Mediated C-H Activation to Form 5- and 6-Membered Palladacycles.钯(II)介导的C-H活化形成五元及六元钯环中的不同动力学/热力学选择性
J Am Chem Soc. 2025 Jul 30;147(30):26091-26096. doi: 10.1021/jacs.5c02735. Epub 2025 Jul 15.
2
Ruthenium Catalyzed Ortho-Arylation Reaction of Benzoic Acids with Arylthianthrenium Salts.钌催化苯甲酸与芳基噻蒽鎓盐的邻位芳基化反应。
Angew Chem Int Ed Engl. 2025 Jun 24;64(26):e202504888. doi: 10.1002/anie.202504888. Epub 2025 May 22.
3
C-H Glycosylation of Native Carboxylic Acids: Discovery of Antidiabetic SGLT-2 Inhibitors.

本文引用的文献

1
Regioselective orthopalladation of (Z)-2-aryl-4-arylidene-5(4H)-oxazolones: scope, kinetico-mechanistic, and density functional theory studies of the C-H bond activation.(Z)-2-芳基-4-芳亚甲基-5(4H)-噁唑啉的区域选择性邻位钯化:C-H 键活化的范围、动理学-机理和密度泛函理论研究。
Inorg Chem. 2011 Sep 5;50(17):8132-43. doi: 10.1021/ic200564d. Epub 2011 Aug 1.
2
Reaction of O2 with [(-)-sparteine]Pd(H)Cl: evidence for an intramolecular [H-L]+ "reductive elimination" pathway.O2 与 [(-)-sparteine]Pd(H)Cl 的反应:支持分子内 [H-L]+“还原消除”途径的证据。
J Am Chem Soc. 2011 Aug 31;133(34):13268-71. doi: 10.1021/ja204989p. Epub 2011 Aug 4.
3
天然羧酸的C-H糖基化:抗糖尿病SGLT-2抑制剂的发现
ACS Cent Sci. 2023 Jun 9;9(6):1129-1139. doi: 10.1021/acscentsci.3c00201. eCollection 2023 Jun 28.
4
Palladium mono--protected amino acid complexes: experimental validation of the ligand cooperation model in C-H activation.单钯保护氨基酸配合物:C-H活化中配体协同模型的实验验证
Chem Sci. 2023 May 26;14(24):6688-6694. doi: 10.1039/d3sc02076b. eCollection 2023 Jun 21.
5
Ligand-Enabled C-H Hydroxylation with Aqueous HO at Room Temperature.在室温下用水相 HO 进行配体促进的 C-H 羟化反应。
J Am Chem Soc. 2022 Oct 5;144(39):18109-18116. doi: 10.1021/jacs.2c08332. Epub 2022 Sep 22.
6
Pd-catalysed C-H functionalisation of free carboxylic acids.钯催化的游离羧酸的C-H官能化反应。
Chem Sci. 2022 Jan 10;13(9):2551-2573. doi: 10.1039/d1sc05392b. eCollection 2022 Mar 2.
7
Mechanism of the Arene-Limited Nondirected C-H Activation of Arenes with Palladium*.钯促进的芳烃非定向 C-H 活化的芳烃限制机制*。
Angew Chem Int Ed Engl. 2021 Jul 5;60(28):15641-15649. doi: 10.1002/anie.202105092. Epub 2021 Jun 9.
8
Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with O.定制醌支持高转化率 Pd 催化剂用于 O 的氧化 C-H 芳基化。
Science. 2020 Dec 18;370(6523):1454-1460. doi: 10.1126/science.abd1085. Epub 2020 Nov 19.
9
Sterically Controlled C-H Olefination of Heteroarenes.位阻控制的杂芳烃 C-H 双键烯烃化反应。
Angew Chem Int Ed Engl. 2020 Jul 13;59(29):12213-12220. doi: 10.1002/anie.202004521. Epub 2020 May 14.
10
Ligand-Enabled γ-C(sp )-H Olefination of Free Carboxylic Acids.配体促进的游离羧酸的γ-C(sp )-H 烯烃化反应。
Angew Chem Int Ed Engl. 2020 Jul 27;59(31):12848-12852. doi: 10.1002/anie.202002362. Epub 2020 May 18.
Silanol: a traceless directing group for Pd-catalyzed o-alkenylation of phenols.
硅醇:一种用于 Pd 催化的酚的邻烯丙基化的无痕迹导向基团。
J Am Chem Soc. 2011 Aug 17;133(32):12406-9. doi: 10.1021/ja204924j. Epub 2011 Jul 21.
4
Direct arylation of polycyclic aromatic hydrocarbons through palladium catalysis.钯催化的多环芳烃的直接芳基化反应。
J Am Chem Soc. 2011 Jul 20;133(28):10716-9. doi: 10.1021/ja202975w. Epub 2011 Jun 23.
5
Regioselective oxidative coupling reactions of 3-substituted thiophenes with arylboronic acids.3-取代噻吩与芳基硼酸的区域选择性氧化偶联反应。
Org Lett. 2011 Jul 15;13(14):3640-3. doi: 10.1021/ol201292v. Epub 2011 Jun 21.
6
Palladium-catalyzed aerobic dehydrogenation of substituted cyclohexanones to phenols.钯催化取代环己酮的有氧脱氢反应生成苯酚。
Science. 2011 Jul 8;333(6039):209-13. doi: 10.1126/science.1204183. Epub 2011 Jun 9.
7
Synthesis of dibenzofurans via palladium-catalyzed phenol-directed C-H activation/C-O cyclization.通过钯催化的酚导向的 C-H 活化/C-O 环化合成二苯并呋喃。
J Am Chem Soc. 2011 Jun 22;133(24):9250-3. doi: 10.1021/ja203335u. Epub 2011 May 31.
8
Cross-coupling of C(sp)-H Bonds with Organometallic Reagents via Pd(II)/Pd(0) Catalysis**.通过钯(II)/钯(0)催化实现C(sp)-H键与有机金属试剂的交叉偶联**。
Isr J Chem. 2010 Dec;50(5-6):605-616. doi: 10.1002/ijch.201000038.
9
Divergent C-H functionalizations directed by sulfonamide pharmacophores: late-stage diversification as a tool for drug discovery.受磺胺类药效团导向的发散性 C-H 官能化反应:晚期多样化作为药物发现的工具。
J Am Chem Soc. 2011 May 11;133(18):7222-8. doi: 10.1021/ja201708f. Epub 2011 Apr 13.
10
Benzoquinone-promoted reaction of O2 with a Pd(II)-hydride.苯醌促进的 O2 与 Pd(II)-氢化物反应。
J Am Chem Soc. 2011 Apr 20;133(15):5732-5. doi: 10.1021/ja200957n. Epub 2011 Mar 25.