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
  • [1] Multicomponent Cascade Synthesis of Trifluoroethyl Isoquinolines from Alkynes and Vinyl Azides
    Liu, Kai
    Chen, Shuang
    Li, Xing Guang
    Liu, Pei Nian
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (01): : 265 - 270
  • [2] Synthesis of Azaheterocycles from Aryl Ketone O-Acetyl Oximes and Internal Alkynes by Cu-Rh Bimetallic Relay Catalysts
    Too, Pei Chui
    Chua, Sze Hui
    Wong, Siong Heng
    Chiba, Shunsuke
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6159 - 6168
  • [3] Acylation of Csp2-H bond with acyl sources derived from alkynes: Rh-Cu bimetallic catalyzed CC bond cleavage
    Xie, Ying
    CHEMICAL COMMUNICATIONS, 2016, 52 (83) : 12372 - 12375
  • [4] Rhodium(III)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes
    Too, Pei Chui
    Wang, Yi-Feng
    Chiba, Shunsuke
    ORGANIC LETTERS, 2010, 12 (24) : 5688 - 5691
  • [5] Rhodium-Catalyzed Oxidative Coupling of Aryl Hydrazones with Internal Alkynes: Efficient Synthesis of Multisubstituted Isoquinolines
    Liu, Wenting
    Hong, Xiaohu
    Xu, Bin
    SYNTHESIS-STUTTGART, 2013, 45 (15): : 2137 - 2149
  • [6] A catalytic approach for the synthesis of allylic azides from aryl vinyl carbinols
    Srinu, G.
    Srihari, P.
    TETRAHEDRON LETTERS, 2013, 54 (19) : 2382 - 2385
  • [7] Rhodium-Catalyzed Synthesis of Isoquinolines and Indenes from Benzylidenehydrazones and Internal Alkynes
    Huang, Xiao-Cheng
    Yang, Xu-Heng
    Song, Ren-Jie
    Li, Jin-Heng
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03): : 1025 - 1031
  • [8] Photochemical Synthesis of Azoarenes from Aryl Azides on Cu(100): A Mechanism Unraveled
    Luo, Yun-Wen
    Chou, Chih-Hung
    Lin, Po-Chiao
    Chiang, Chao-Ming
    JOURNAL OF PHYSICAL CHEMISTRY C, 2019, 123 (19): : 12195 - 12202
  • [9] Synthesis of aryl azides from aryl halides promoted by Cu2O/tetraethylammonium prolinate
    Hajipour, Abdol R.
    Mohammadsaleh, Fatemeh
    TETRAHEDRON LETTERS, 2014, 55 (50) : 6799 - 6802
  • [10] Nickel-catalysed synthesis of tetrasubstituted vinyl sulfides from thiocarbamates and internal alkynes
    Inami, Tasuku
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMICAL COMMUNICATIONS, 2015, 51 (07) : 1285 - 1288