Synthesis of diynes from 1-(2,2-dibromovinyl)-2-(phenylethynyl)benzene and imidazole/benzimidazole via a CuI/Pd(OAc)2 catalysed cascade reaction

被引：3
|
作者：
He Hua-Feng [1 ,2 ,3 ]
Ye Yang [1 ,2 ,3 ]
Jiang Yongwen [1 ,2 ,3 ]
Bao Weiliang [4 ]
机构：
[1] Chinese Acad Agr Sci, Tea Res Inst, Hangzhou 310008, Zhejiang, Peoples R China
[2] Minist Agr, Key Lab Tea Biol & Resources Utilizat, Hangzhou 310008, Zhejiang, Peoples R China
[3] Natl Engn Technol Res Ctr Tea Ind, Hangzhou 310008, Zhejiang, Peoples R China
[4] Zhejiang Univ, Dept Chem, Hangzhou 310008, Zhejiang, Peoples R China
来源：
JOURNAL OF CHEMICAL RESEARCH | 2014年 / 07期
关键词：
diynes; 1-(2,2-dibromovinyl)-2-(phenylethynyl)benzene; imidazole; elimination; Ullmann-type coupling; COUPLING REACTIONS; MODULAR SYNTHESIS; NATURAL-PRODUCTS; C-C; DERIVATIVES; ARYL;
D O I：
10.3184/174751914X14019525018744
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A novel reaction between 1-(2,2-dibromovinyl)-2-(phenylethynyl)benzene and imidazole/benzimidazole catalysed by CuI and Pd(OAc)(2) gave the corresponding highly sterically hindered diynes via a cascade elimination/Ullmann-type C-N coupling process.
引用
收藏
页码：399 / 403
页数：5
相关论文
共 50 条
  • [1] Synthesis of 2-(Polyfluoroaryl)benzofurans via a Copper(I)-Catalyzed Reaction of 2-(2,2-Dibromovinyl)phenol with Polyfluoroarene
    Ye, Shengqing
    Liu, Gang
    Pu, Shouzhi
    Wu, Jie
    ORGANIC LETTERS, 2012, 14 (01) : 70 - 73
  • [2] Crystal Structure of 2-(2,2-Dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
    Jan Lokaj
    Jan Moncol
    Filip Bureš
    Jiří Kulhánek
    Journal of Chemical Crystallography, 2011, 41 : 834 - 837
  • [3] Crystal Structure of 2-(2,2-Dibromovinyl)-1-methyl-1H-imidazole-4,5-dicarbonitrile
    Lokaj, Jan
    Moncol, Jan
    Bures, Filip
    Kulhanek, Jiri
    JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 2011, 41 (06) : 834 - 837
  • [4] Electrochemically modified Corey-Fuchs reaction for the synthesis of arylalkynes. The case of 2-(2,2-dibromovinyl)naphthalene
    Pandolfi, Fabiana
    Chiarotto, Isabella
    Feroci, Marta
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 : 891 - 899
  • [5] Palladium-Catalyzed Carbonylative Reaction of 1-(2,2-Dibromovinyl)-2-alkenylbenzene and Carbon Monoxide, with Phenol or Alcohol
    Ye, Shengqing
    Wu, Jie
    ORGANIC LETTERS, 2011, 13 (22) : 5980 - 5983
  • [6] One-Pot Synthesis of 3-Halo-2-organochalcogenylbenzo[b] chalcogenophenes from 1-(2,2-Dibromovinyl)-2-organochalcogenylbenzenes
    Luz, Eduardo Q.
    Silverio, Gabriel L.
    Seckler, Diego
    Lima, David B.
    Santana, Francielli S.
    Barbosa, Ronilson V.
    Montes D'Oca, Caroline R.
    Rampon, Daniel S.
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (10) : 2610 - 2618
  • [7] Synthesis of 2-Organylchalcogenyl-benzo[b]selenophenes: 1-(2,2-Dibromovinyl)-2-butylselenanylbenzenes as Precursors to Access Alkynes Susceptible to Cyclization
    Perin, Gelson
    Roehrs, Juliano A.
    Hellwig, Paola S.
    Stach, Guilherme
    Barcellos, Thiago
    Lenardao, Eder J.
    Jacob, Raquel G.
    Luz, Eduardo Q.
    CHEMISTRYSELECT, 2017, 2 (16): : 4561 - 4566
  • [8] Efficient Assembly of 1-Methylene-1H-indenes via Palladium-Catalyzed Tandem Reaction of 1-(2,2-Dibromovinyl)-2-alkenylbenzene with Arylboronic Acid
    Ye, Shengqing
    Ren, Hui
    Wu, Jie
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (05): : 670 - 675
  • [9] Regioselective Fluorination of 1-(2,2-Dibromovinyl)benzene Derivatives with Wet Tetra-n-butylammonium Fluoride: One-Pot Synthesis of (Z)-1-(2-Bromo-1-fluorovinyl)benzenes
    Zhao, Mingzhu
    Ming, Ling
    Tang, Jialiang
    Zhao, Xiaoming
    ORGANIC LETTERS, 2016, 18 (03) : 416 - 419
  • [10] Rapid access to 1-methyleneindenes via palladium-catalyzed tandem reactions of 1-(2,2-dibromovinyl)-2-alkynylbenzenes with arylboronic acids
    Ye, Shengqing
    Yang, Xiaodi
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2010, 46 (17) : 2950 - 2952
12345