• 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

使用铜催化β-酮膦酸酯的α-芳基化和脱酰基α-芳基化合成α-芳基膦酸酯

Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

作者信息

Rout Laxmidhar, Regati Sridhar, Zhao Cong-Gui

机构信息

Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249, USA.

出版信息

Adv Synth Catal. 2011 Dec 1;353(18):3340-3346. doi: 10.1002/adsc.201100605. Epub 2011 Dec 6.

DOI:10.1002/adsc.201100605
PMID:22505878
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3324819/
Abstract

Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts were developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data.

摘要

开发了在铜(I)或铜(II)盐作为催化剂存在下,β-酮膦酸酯与碘代芳烃直接芳基化和脱酰基芳基化的有效方法。以高收率得到了相应的α-芳基膦酸酯。根据实验数据提出了脱酰基芳基化反应的初步机理。

相似文献

1
Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.使用铜催化β-酮膦酸酯的α-芳基化和脱酰基α-芳基化合成α-芳基膦酸酯
Adv Synth Catal. 2011 Dec 1;353(18):3340-3346. doi: 10.1002/adsc.201100605. Epub 2011 Dec 6.
2
Access to Chiral HWE Reagents by Rhodium-Catalyzed Asymmetric Arylation of γ,δ-Unsaturated β-Ketophosphonates.通过铑催化不对称芳基化γ,δ-不饱和β-酮膦酸酯实现手性 HWE 试剂的获得。
J Org Chem. 2018 May 18;83(10):5869-5875. doi: 10.1021/acs.joc.8b00952. Epub 2018 May 7.
3
Palladium- and copper-catalyzed arylation of carbon-hydrogen bonds.钯和铜催化的碳氢键芳基化反应。
Acc Chem Res. 2009 Aug 18;42(8):1074-86. doi: 10.1021/ar9000058.
4
Zwitterion-Catalyzed Deacylative Dihalogenation of β-Oxo Amides.两性离子催化的β-羰基酰胺脱酰基二卤化反应。
Org Lett. 2020 Sep 18;22(18):7353-7357. doi: 10.1021/acs.orglett.0c02701. Epub 2020 Sep 1.
5
Proline/pipecolinic acid-promoted copper-catalyzed P-arylation.脯氨酸/哌啶酸促进的铜催化P-芳基化反应
J Org Chem. 2006 Jun 23;71(13):5020-2. doi: 10.1021/jo060492j.
6
Synthesis of unsymmetrical 2,2'-biindolyl derivatives by a Cu-catalyzed N-arylation/Pd-catalyzed direct arylation sequential process.通过 Cu 催化的 N-芳基化/Pd 催化的直接芳基化顺序反应合成不对称 2,2'-联吲哚衍生物。
J Org Chem. 2011 Feb 4;76(3):967-70. doi: 10.1021/jo101899a. Epub 2011 Jan 12.
7
Copper-catalyzed tandem cyclization/arylation of α,β-alkynic hydrazones with diaryliodonium salts: synthesis of -arylpyrazoles.铜催化α,β-炔基腙与二芳基碘鎓盐的串联环化/芳基化反应:-芳基吡唑的合成
Org Biomol Chem. 2023 Jul 19;21(28):5784-5789. doi: 10.1039/d3ob00899a.
8
O-arylation versus C-arylation: copper-catalyzed intramolecular coupling of aryl bromides with 1,3-dicarbonyls.氧芳基化与碳芳基化:铜催化芳基溴化物与1,3 - 二羰基化合物的分子内偶联反应
J Org Chem. 2006 Aug 18;71(17):6427-31. doi: 10.1021/jo060747t.
9
Deacylative arylation and alkynylation of unstrained ketones.未环张力酮的脱酰芳基化和炔基化反应
Sci Adv. 2024 Apr 26;10(17):eado0225. doi: 10.1126/sciadv.ado0225.
10
N-Arylation of amines, amides, imides and sulfonamides with arylboroxines catalyzed by simple copper salt/EtOH system.简单的铜盐/乙醇体系催化的芳基硼酸与胺、酰胺、酰亚胺和磺酰胺的 N-芳基化反应。
Beilstein J Org Chem. 2008;4:40. doi: 10.3762/bjoc.4.40. Epub 2008 Nov 7.

引用本文的文献

1
Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination.通往α-芳基膦酰基乙酸酯的路线:霍纳-沃兹沃思-埃蒙斯烯烃化反应中有用的合成前体。
J Org Chem. 2015 Oct 16;80(20):10288-93. doi: 10.1021/acs.joc.5b01887. Epub 2015 Oct 3.
2
Palladium-catalyzed α-arylation of benzylic phosphonates.钯催化的苄基膦酸酯的α-芳基化反应。
Org Lett. 2014 Mar 7;16(5):1446-9. doi: 10.1021/ol5002413. Epub 2014 Feb 12.
3
Palladium-catalyzed α-arylation of benzylic phosphine oxides.钯催化的苄基膦氧化物的α-芳基化反应。
Org Lett. 2014 Jan 3;16(1):130-3. doi: 10.1021/ol403124g. Epub 2013 Dec 2.

本文引用的文献

1
Quinidine thiourea-catalyzed enantioselective synthesis of β-nitrophosphonates: Beneficial effects of molecular sieves.奎尼丁硫脲催化的β-硝基膦酸酯对映选择性合成:分子筛的有益作用
Tetrahedron. 2011 Sep 30;67(39):7479-7484. doi: 10.1016/j.tet.2011.07.059.
2
Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.有机催化高对映选择性合成β-甲酰基-α-羟基膦酸酯
Adv Synth Catal. 2011 Jun 30;353(10):1729-1734. doi: 10.1002/adsc.201000835.
3
Direct conversion of benzylic and allylic alcohols to phosphonates.苄基和烯丙醇直接转化为膦酸酯。
J Org Chem. 2011 Apr 15;76(8):2875-9. doi: 10.1021/jo200137k. Epub 2011 Mar 15.
4
Copper catalyzed arylation/C-C bond activation: an approach toward alpha-aryl ketones.铜催化芳基化/C-C 键活化:一种合成α-芳基酮的方法。
J Am Chem Soc. 2010 Jun 23;132(24):8273-5. doi: 10.1021/ja1033777.
5
Rhodium-catalyzed C-C bond cleavage: construction of acyclic methyl substituted quaternary stereogenic centers.铑催化的 C-C 键断裂:构建非环甲基取代的季立体中心。
J Am Chem Soc. 2010 Apr 21;132(15):5340-1. doi: 10.1021/ja101469t.
6
Organocatalytic enantioselective synthesis of both diastereomers of alpha-hydroxyphosphinates.有机催化对映选择性合成α-羟基膦酸盐的两种非对映异构体。
J Org Chem. 2010 Feb 19;75(4):1101-6. doi: 10.1021/jo9022099.
7
Rh-catalyzed Negishi alkyl-aryl cross-coupling leading to alpha- or beta-phosphoryl-substituted alkylarenes.铑催化的根岸烷基-芳基交叉偶联反应生成α-或β-磷酰基取代的烷基芳烃。
J Org Chem. 2009 Apr 3;74(7):2794-7. doi: 10.1021/jo900142b.
8
Inhibition of purple acid phosphatase with alpha-alkoxynaphthylmethylphosphonic acids.用α-烷氧基萘基甲基膦酸抑制紫色酸性磷酸酶。
Bioorg Med Chem Lett. 2009 Jan 1;19(1):163-6. doi: 10.1016/j.bmcl.2008.10.125. Epub 2008 Nov 5.
9
Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.铜/氨基酸催化的芳基卤化物和乙烯基卤化物与亲核试剂的交叉偶联反应。
Acc Chem Res. 2008 Nov 18;41(11):1450-60. doi: 10.1021/ar8000298.
10
Enantioselective synthesis of alpha-aminopropargylphosphonates.α-氨基炔丙基膦酸酯的对映选择性合成
Tetrahedron Lett. 2007 Jun 18;48(25):4339-4342. doi: 10.1016/j.tetlet.2007.04.124.