Reactions of alkynes with trisubstituted (Z)-bromoalkenyl-pinacolboronates towards the synthesis of 1,2,4,6-tetrasubstituted benzenes

被引：3
|
作者：
Yalagala, Ravi Shekar [1 ]
Yan, Hongbin [1 ]
机构：
[1] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 34期
关键词：
Tetrasubstituted benzene; Aromatization; Bromoalkene pinacolboronate; Terminal alkyne; Cyclization; TERMINAL ALKYNES; 1,2,4,5-TETRASUBSTITUTED BENZENES; TETRASUBSTITUTED BENZENES; BENZANNULATION; DERIVATIVES;
D O I：
10.1016/j.tetlet.2014.07.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of trisubstituted (Z)-bromoalkenyl-pinacolboronates with terminal alkynes in the presence of cuprous iodide, palladium(0) tetrakis(triphenylphosphine) and Hunig's base leads to the formation of 1,2,4,6-tetrasubstituted aromatic compounds in a one-pot fashion. Substrate scope was shown for three trisubstituted (Z)-bromoalkenyl-pinacolboronates and four terminal alkynes. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4830 / 4832
页数：3
相关论文
共 50 条
  • [31] Synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted-1H-imidazole derivatives and or 2,4,5-Triaryloxazoles using of Silica-Supported Preyssler Nanoparticles
    Gharib, A.
    Khorasani, B. R. H. Hashemipour
    Jahangir, M.
    Roshani, M.
    Bakhtiari, L.
    Mohadeszadeh, S.
    BULGARIAN CHEMICAL COMMUNICATIONS, 2014, 46 (01): : 165 - 174
  • [32] Synthesis of 5-methylene-1,3-cyclohexadienes (o-isotoluenes) via electrocyclization of (4Z)-1,2,4,6-heptatetraenes
    Wang, KK
    Zhang, Q
    Liao, JK
    TETRAHEDRON LETTERS, 1996, 37 (24) : 4087 - 4090
  • [33] Tandem Reaction of 1-Copper(I) Alkynes for the Synthesis of 1,4,5-Trisubstituted 5-Chloro-1,2,3-triazoles
    Wang, Bo
    Zhang, Jianlan
    Wang, Xinyan
    Liu, Nan
    Chen, Wenwen
    Hu, Yuefei
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20): : 10519 - 10523
  • [34] An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed via solid acid nano-catalyst
    Teimouri, Abbas
    Chermahini, Alireza Najafi
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2011, 346 (1-2) : 39 - 45
  • [35] L-Proline triflate as an efficient and reusable catalyst for the one-pot synthesis of 2,4,5-trisubstituted imidazoles and 1,2,4,5-tetrasubstituted imidazoles
    Li, Jianjun
    Lin, Shouwang
    Dai, Jiajia
    Su, Weike
    JOURNAL OF CHEMICAL RESEARCH, 2010, (04) : 196 - 199
  • [36] An efficient multicomponent synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by a magnetic nanoparticle supported Lewis acidic deep eutectic solvent
    Nguyen, Thanh Thi
    Le, Ngoc-Phuong Thi
    Nguyen, The Thai
    Tran, Phuong Hoang
    RSC ADVANCES, 2019, 9 (65) : 38148 - 38153
  • [37] REACTIONS OF AZOMETHINE DERIVATIVES .4. SYNTHESIS OF 2,3,5-TRISUBSTITUTED 2-PYRROLIN-4-ONES AND THEIR OXIDATION TO 2,4,5-TRISUBSTITUTED 1,3-OXAZIN-6-ONES
    TAKAHASHI, M
    INABA, N
    KIRIHARA, H
    WATANABE, SI
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (11) : 3312 - 3315
  • [38] Synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by copper-catalyzed cycloaddition-coupling of azides and terminal alkynes
    Gerard, Baudouin
    Ryan, Jamie
    Beeler, Aaron B.
    Porco, John A., Jr.
    TETRAHEDRON, 2006, 62 (26) : 6405 - 6411
  • [39] Synthesis of 4,6-disubstituted- and 4,5,6-trisubstituted-2-phenyl-pyrimidines and their affinity towards A(1) adenosine receptors
    Biagi, G
    Giorgi, I
    Livi, O
    Scartoni, V
    Lucacchini, A
    FARMACO, 1997, 52 (01): : 61 - 65
  • [40] An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3•3H2O
    Das Sharma, Salkat
    Hazarika, Parasa
    Konwar, Dilip
    TETRAHEDRON LETTERS, 2008, 49 (14) : 2216 - 2220
12345