Exploratory Studies on the Reaction Between Iodoarenes and Acetylenes: One-pot, Pd-[Bmim][BF4] Catalyzed Preparation of Trianisylethylene

被引：5
作者：
Barros, Jose C. [1 ]
Souza, Andrea L. F. [1 ]
da Silva, Joaquim F. M. [1 ]
Antunes, O. A. C. [1 ]
机构：
[1] Univ Fed Rio de Janeiro, Inst Quim, BR-21941909 Rio De Janeiro, Brazil
来源：
CATALYSIS LETTERS | 2011年 / 141卷 / 04期
关键词：
Sonogashira reaction; Hydroarylation; SERM; ALKYNE HYDROARYLATION; ARYL IODIDES; EFFICIENT; ALCOHOLS; SELECTIVITY; ROUTE; DI;
D O I：
10.1007/s10562-011-0549-7
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
The reaction between iodoarenes and acetylenes mediated by palladium was studied, showing selectivity changes based on the nature of the substituent. A new, phosphine-, copper-, and amine-free methodology was developed, in which the synthesis of trianisylethylene from 4-iodoanisole and trimethylsilylacetylene was promoted presumably by an N-heterocyclic-carbene derived from an ionic liquid and a palladium salt, using ethanol as the hydrogen source.
引用
收藏
页码：549 / 553
页数：5
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  • [1] THE PALLADIUM-CATALYZED REDUCTIVE ADDITION OF ARYL IODIDES TO PROPARGYL ALCOHOLS - A ROUTE TO GAMMA,GAMMA-DIARYL ALLYLIC ALCOHOLS
    ARCADI, A
    CACCHI, S
    MARINELLI, F
    [J]. TETRAHEDRON, 1985, 41 (22) : 5121 - 5131
  • [2] CHEMICALLY EFFICIENT AZA-DI-PI-METHANE PHOTOREACTIVITY WITH NOVEL STABLE DERIVATIVES OF BETA,GAMMA-UNSATURATED CARBONYL-COMPOUNDS
    ARMESTO, D
    HORSPOOL, WM
    MANCHENO, MJ
    ORTIZ, MJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18): : 2325 - 2329
  • [3] The α-arylation of α-bromo- and α-chloroenones using palladium-catalysed cross-coupling
    Banks, JC
    Van Mele, D
    Frost, CG
    [J]. TETRAHEDRON LETTERS, 2006, 47 (17) : 2863 - 2866
  • [4] Selectivity studies in the reaction between iodobenzene and phenylacetylene: Sonogashira coupling vs hydroarylation
    Barros, Jose C.
    de Souza, Andrea Luzia F.
    de Lima, Paulo G.
    da Silva, Joaquim F. M.
    Antunes, O. A. C.
    [J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2008, 22 (05) : 249 - 252
  • [5] Aryl Norbornanes and Analogues via Palladium-Catalyzed Hydroarylation with Arenediazonium Tetrafluoroborates
    Bartoli, Gabriele
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    [J]. SYNLETT, 2008, (16) : 2508 - 2512
  • [6] Highly efficient alkyne hydroarylation with Chelating dicarbene Palladium(II) and Platinum(II) complexes
    Biffis, Andrea
    Tubaro, Cristina
    Buscemi, Gabriella
    Basato, Marino
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (01) : 189 - 196
  • [7] Development of a palladium catalyzed addition of boronic acids to alkynyl esters: synthesis of trisubstituted olefins as single isomers
    Bush, Alexander Graham
    Jiang, Jojo Liu
    Payne, Philippa R.
    Ogilvie, William W.
    [J]. TETRAHEDRON, 2009, 65 (41) : 8502 - 8506
  • [8] The palladium-catalyzed hydroarylation of propargylic alcohols in room temperature ionic liquids
    Cacchi, S
    Fabrizi, G
    Goggiamani, A
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2004, 214 (01) : 57 - 64
  • [9] Palladium-catalyzed hydroarylation of alkynes with arenediazonium salts
    Cacchi, Sandro
    Fabrizi, Giancarlo
    Goggiamani, Antonella
    Persiani, Daniela
    [J]. ORGANIC LETTERS, 2008, 10 (08) : 1597 - 1600
  • [10] Ethynyl-cyclohexanol:: an efficient acetylene surrogate in Sonogashira coupling
    Csekei, Marton
    Novak, Zoltan
    Kotschy, Andras
    [J]. TETRAHEDRON, 2008, 64 (06) : 975 - 982
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