Regiospecific Functionalization of Azacalixaromatics through Copper-Mediated Aryl C-H Activation and C-O Bond Formation

被引:64
|
作者
Wang, Zu-Li [1 ]
Zhao, Liang [1 ]
Wang, Mei-Xiang [1 ]
机构
[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Organ Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China
关键词
PI INTERACTIONS; EN-ROUTE; RECOGNITION; CAVITY; OXACALIXARENES; COMPLEXATION; 1,3-ALTERNATE; RECEPTORS; CAGE;
D O I
10.1021/ol202874n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regiospecific functionalization of tetraazacalix[1]arene[3]pyridines at the lower rim position of the benzene ring was achieved conveniently from their cross-coupling reaction with both aliphatic alcohols including chiral primary and secondary alcohols and phenol derivatives through the Cu(ClO4)(2)-mediated aerobic aryl C-H activation, which gave structurally well-defined aryl-Cu(III) intermediates and a subsequent C-O bond formation reaction under very mild conditions.
引用
收藏
页码:6560 / 6563
页数:4
相关论文
共 50 条
  • [1] Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C-H Functionalization/C-N/C-O Bond Formation
    Guru, Murali Mohan
    Ali, Md Ashif
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (13): : 5295 - 5308
  • [2] Synthesis of benzoxazoles by copper-catalyzed regioselective C-H functionalization/C-O bond formation
    Ueda, Satoshi
    Nagasawa, Hideko
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [3] Copper-mediated selective oxidation of a C-H bond
    Boldron, C
    Gamez, P
    Tooke, DM
    Spek, AL
    Reedijk, J
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (23) : 3585 - 3587
  • [4] Divergent copper-mediated dimerization and hydroxylation of benzamides involving C-H bond functionalization
    Wang, Mingliang
    Hu, Yimin
    Jiang, Zhe
    Shen, Hong C.
    Sun, Xun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (18) : 4239 - 4246
  • [5] Modern synthetic methods for copper-mediated C(aryl)-O, C(aryl)-N, and C(aryl)-S bond formation
    Ley, SV
    Thomas, AW
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (44) : 5400 - 5449
  • [6] Substrate scope study of tandem acyl C-O/aryl C-H bond activation
    Gemmel, Philipp
    Anderson, Constance
    Serratore, Nicholas
    Underwood, Steven
    Douglas, Christopher
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [7] Copper-Catalyzed Oxidative C-H Bond Functionalization of N-Allylbenzamide for Regioselective C-N and C-O Bond Formation
    Ranjith, Jala
    Krishna, Palakodety Radha
    CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (09) : 1448 - 1451
  • [8] Regioselective C-H Activation and Sequential C-C and C-O Bond Formation Reactions of Aryl Ketones Promoted by an Yttrium Carbene
    Mills, David P.
    Soutar, Lyndsay
    Lewis, William
    Blake, Alexander J.
    Liddle, Stephen T.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (41) : 14379 - 14381
  • [9] Organocatalytic Syntheses of Benzoxazoles and Benzothiazoles using Aryl Iodide and Oxone via C-H Functionalization and C-O/S Bond Formation
    Alla, Santhosh Kumar
    Sadhu, Pradeep
    Punniyamurthy, Tharmalingam
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16): : 7502 - 7511
  • [10] Frustrated Lewis pair-mediated C-O or C-H bond activation of ethers
    Holthausen, Michael H.
    Mahdi, Tayseer
    Schlepphorst, Christoph
    Hounjet, Lindsay J.
    Weigand, Jan J.
    Stephan, Douglas W.
    CHEMICAL COMMUNICATIONS, 2014, 50 (70) : 10038 - 10040