Synthesis of Isoquinolines from α-Aryl Vinyl Azides and Internal Alkynes by Rh-Cu Bimetallic Cooperation

被引:274
|
作者
Wang, Yi-Feng [1 ]
Toh, Kah Kah [1 ]
Lee, Jian-Yuan [1 ]
Chiba, Shunsuke [1 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
关键词
alkynes; azides; copper; heterocycles; rhodium; CATALYZED OXIDATIVE COUPLING/CYCLIZATION; FREE-RADICAL REACTIONS; BOND FORMATION; CARBON-HYDROGEN; FUNCTIONALIZATION; BENZAMIDES; COMPLEXES; PYRROLES; IMINES; RU;
D O I
10.1002/anie.201101009
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Catalysts in a relay: A synthetic method for delivering highly substituted isoquinolines has been developed (see scheme; Cp =C5Me5, DMF=N,N-dimethylformamide, TEMPO=2,2,6,6-tetramethylpiperidine-1-oxyl). A preliminary mechanistic study showed that the rhodium and copper cooperate synergistically in the multistep sequence. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5927 / 5931
页数:5
相关论文
共 31 条
  • [21] Four-component coupling reactions of silylacetylenes, allyl carbonates, and trimethylsilyl azide catalyzed by a Pd(0)-Cu(I) bimetallic catalyst. Fully substituted triazole synthesis from seemingly internal alkynes
    Kamijo, S
    Jin, T
    Yamamoto, Y
    TETRAHEDRON LETTERS, 2004, 45 (04) : 689 - 691
  • [22] Synthesis of triazoles from nonactivated terminal alkynes via the three-component coupling reaction using a Pd(0)-Cu(I) bimetallic catalyst
    Kamijo, S
    Jin, TN
    Huo, ZB
    Yamamoto, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (26) : 7786 - 7787
  • [23] Cooperative Pd/Cu Catalysis: Multicomponent Synthesis of Tetrasubstituted Imidazolones from Methyl a-lsocyanoacetates, Primary Amines, and Aryl(vinyl) Iodides
    Clemenceau, Antonin
    Wang, Qian
    Zhu, Jieping
    ORGANIC LETTERS, 2018, 20 (01) : 126 - 129
  • [24] Synthesis of 2-Alkoxyaryl-2-aryl Enamines via Tandem Copper-Catalyzed Cycloaddition and Rhodium-Catalyzed Alkoxyarylation from Alkynes, N-Sulfonyl Azides, and Aryl Ethers (vol 80, pg 5859, 2015)
    Shin, Seohyun
    Park, Youngchul
    Kim, Cheol-Eui
    Son, Jeong-Yu
    Lee, Phil Ho
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9803 - 9803
  • [25] Substituent-controlled selective synthesis of 1,2-diketones and internal alkynes from terminal alkynes and arylboronic acids via α-stilbene radicals obtained from heteroleptic Cu(i) complexes under visible light
    Neerathilingam, Nalladhambi
    Prasanth, Kesavan
    Anandhan, Ramasamy
    GREEN CHEMISTRY, 2022, 24 (22) : 8685 - 8690
  • [26] Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C-H Annulation
    Jagtap, Prafull A.
    Lokolkar, Manjunath S.
    Bhanage, Bhalchandra M.
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (15): : 10960 - 10973
  • [27] One-Pot Synthesis of Multisubstituted 2-Aminoquinolines from Annulation of 1-Aryl Tetrazoles with Internal Alkynes via Double C-H Activation and Denitrogenation
    Zhang, Lei
    Zheng, Liyao
    Guo, Biao
    Hua, Ruimao
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11541 - 11548
  • [28] Zirconium-mediated selective synthesis of 1,4-dialkyl(aryl)-hexa-substituted benzenes from two silyl-substituted alkynes and one internal alkyne
    Junqiu Li
    Jiqian Zhang
    Hongmei Qu
    Jun Liu
    Juan Li
    Lishan Zhou
    Chemical Research in Chinese Universities, 2016, 32 : 366 - 372
  • [29] Zirconium-mediated Selective Synthesis of 1,4-Dialkyl(aryl)-hexa-substituted Benzenes from Two Silyl-substituted Alkynes and One Internal Alkyne
    Li Junqiu
    Zhang Jiqian
    Qu Hongmei
    Liu Jun
    Li Juan
    Zhou Lishan
    CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2016, 32 (03) : 366 - 372
  • [30] Cu-N-heterocyclic carbene-catalysed synthesis of 2-aryl-3-(arylethynyl)quinoxalines from one-pot tandem coupling of o-phenylenediamines and terminal alkynes
    Motakatla, Venkata Krishna Reddy
    Gokanapalli, Anusha
    Peddiahgari, Vasu Govardhana Reddy
    APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (11)