Heterogeneous heck coupling in multivariate metal-organic frameworks for enhanced selectivity

被引:24
作者
Brown, Jonathan W. [1 ]
Jarenwattananon, Nanette N. [1 ]
Otto, Trenton [1 ]
Wang, James L. [1 ]
Gloeggler, Stefan [1 ]
Bouchard, Louis-S. [1 ]
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
基金
美国国家科学基金会;
关键词
Metal-organic framework; Heterogeneous catalyst; Heck coupling; Resveratrol; PALLADIUM; CATALYSTS; DESIGN; RESVERATROL; MOFS;
D O I
10.1016/j.catcom.2015.03.005
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
Highly selective heterogeneous Heck coupling has been demonstrated inside a series of metal-organic frameworks (MOFs). These MOFs, Zn4O(BDC-NH2)(n)(BDC)((3 - n)) (n = 3, 2.4, 1.8, 1.2, 0.9, 0.75, 0.6, 0.3, and 0.15), have been synthesized with different amounts of 1,4-benzenedicarboxylate (BDC) and 2-amino-1,4-benzenedicarboxylate (BDC-NH2) incorporated into their structure. The BDC-NH2 is functionalized by covalent postmodification with salicylic aldehyde for binding catalytically active Pd(II) ions. The catalytic activity of the embedded Pd(II) ions was tested via heterogeneous Heck coupling to produce resveratrol trimethyl ether, a pharmaceutically relevant precursor. It is also found during catalytic testing that a trade-off exists between amount of metalation and pore blocking. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:105 / 107
页数:3
相关论文
共 36 条
[1]   Synthesis of methylated resveratrol and analogues by Heck reactions in organic and aqueous solvents [J].
Botella, L ;
Nájera, C .
TETRAHEDRON, 2004, 60 (26) :5563-5570
[2]  
Bradamante S, 2004, CARDIOVASC DRUG REV, V22, P169
[3]   Knoevenagel Condensation Reactions Catalysed by Metal-Organic Frameworks [J].
Burgoyne, Andrew R. ;
Meijboom, Reinout .
CATALYSIS LETTERS, 2013, 143 (06) :563-571
[4]   Post-Synthetic Modification of Tagged Metal-Organic Frameworks [J].
Burrows, Andrew D. ;
Frost, Christopher G. ;
Mahon, Mary F. ;
Richardson, Christopher .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (44) :8482-8486
[5]   A molecular Pd(II) complex incorporated into a MOF as a highly active single-site heterogeneous catalyst for C-Cl bond activation [J].
Chen, Liyu ;
Rangan, Sylvie ;
Li, Jing ;
Jiang, Huanfeng ;
Li, Yingwei .
GREEN CHEMISTRY, 2014, 16 (08) :3978-3985
[6]   Synthesis, X-ray crystal structures, and gas sorption properties of pillared square grid nets based on paddle-wheel motifs: Implications for hydrogen storage in porous materials [J].
Chun, H ;
Dybtsev, DN ;
Kim, H ;
Kim, K .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (12) :3521-3529
[7]   Basic zeolites containing palladium as bifunctional heterogeneous catalysts for the Heck reaction [J].
Corma, A ;
García, H ;
Leyva, A ;
Primo, A .
APPLIED CATALYSIS A-GENERAL, 2003, 247 (01) :41-49
[8]   Resolving Heterogeneity Problems and Impurity Artifacts in Operationally Homogeneous Transition Metal Catalysts [J].
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2012, 112 (03) :1536-1554
[9]   Multiple Functional Groups of Varying Ratios in Metal-Organic Frameworks [J].
Deng, Hexiang ;
Doonan, Christian J. ;
Furukawa, Hiroyasu ;
Ferreira, Ricardo B. ;
Towne, John ;
Knobler, Carolyn B. ;
Wang, Bo ;
Yaghi, Omar M. .
SCIENCE, 2010, 327 (5967) :846-850
[10]   Isoreticular Metalation of Metal-Organic Frameworks [J].
Doonan, Christian J. ;
Morris, William ;
Furukawa, Hiroyasu ;
Yaghi, Omar M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (27) :9492-+