Diethanolamine and N,N-diethylethanolamine ionic liquids as precatalyst-precursors and reaction media in green Heck reaction protocol

被引:25
作者
Petrovic, Zorica D. [1 ]
Simijonovic, Dusica [1 ]
Petrovic, Vladimir P. [1 ]
Markovic, Svetlana [1 ]
机构
[1] Univ Kragujevac, Fac Sci, Kragujevac 34000, Serbia
关键词
Heck reaction; Diethanolamine and N; N-diethylethanolamine ionic liquids; Pd precatalyst; Biphasic catalysis; PALLADIUM CATALYST PRECURSOR; RECYCLABLE CATALYST; OXIDATIVE ADDITION; PHOSPHINE-LIGANDS; HIGHLY EFFICIENT; CARBENE; HYDROFORMYLATION; ARYLATION; SOLVENTS; COMPLEX;
D O I
10.1016/j.molcata.2010.05.010
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
It was found that Heck reaction with PdCl2 in diethanolamine and N,N-diethylethanolamine ionic liquids (ILs) is more efficient than analogous reactions performed in classical organic solvents. The used Its facilitate solubility of the Pd(II) precatalysts, increase catalyst stability during the reaction, and function as reaction media, bases, precatalyst-precursors, good coordinating ligands, and mobile support for active Pd species. Thus, Heck reaction occurs without additional solvents, ligands and bases, that makes experimental procedure much simpler. Our DFT investigation provides mechanistic insight into the formation of the trans-[PdCl2(DEA)(2)] complex that acts as a precatalyst. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:45 / 50
页数:6
相关论文
共 63 条
  • [1] ROLE AND EFFECTS OF HALIDE-IONS ON THE RATES AND MECHANISMS OF OXIDATIVE ADDITION OF IODOBENZENE TO LOW-LIGATED ZEROVALENT PALLADIUM COMPLEXES PD0(PPH3)2
    AMATORE, C
    AZZABI, M
    JUTAND, A
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) : 8375 - 8384
  • [2] Structure and properties of high stability geminal dicationic ionic liquids
    Anderson, JL
    Ding, RF
    Ellern, A
    Armstrong, DW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 593 - 604
  • [3] Imidazolylidenes, imidazolinylidenes and imidazolidines
    Arduengo, AJ
    Krafczyk, R
    Schmutzler, R
    Craig, HA
    Goerlich, JR
    Marshall, WJ
    Unverzagt, M
    [J]. TETRAHEDRON, 1999, 55 (51) : 14523 - 14534
  • [4] An ionic liquid-supported ruthenium carbene complex: A robust and recyclable catalyst for ring-closing olefin metathesis in ionic liquids
    Audic, N
    Clavier, H
    Mauduit, M
    Guillemin, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (31) : 9248 - 9249
  • [5] CO2 capture by a task-specific ionic liquid
    Bates, ED
    Mayton, RD
    Ntai, I
    Davis, JH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (06) : 926 - 927
  • [6] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE
    BECKE, AD
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) : 5648 - 5652
  • [7] DENSITY-FUNCTIONAL EXCHANGE-ENERGY APPROXIMATION WITH CORRECT ASYMPTOTIC-BEHAVIOR
    BECKE, AD
    [J]. PHYSICAL REVIEW A, 1988, 38 (06): : 3098 - 3100
  • [8] Böhm VPW, 2000, CHEM-EUR J, V6, P1017, DOI 10.1002/(SICI)1521-3765(20000317)6:6<1017::AID-CHEM1017>3.0.CO
  • [9] 2-8
  • [10] Brase S, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P99