Palladium Acetate/[CPy][Br]: An Efficient Catalytic System towards the Synthesis of Biologically Relevant Stilbene Derivatives via Heck Cross-Coupling Reaction.

被引:14
作者
Girase, Tejpalsingh Ramsingh [1 ]
Patil, Kesharsingh J. [2 ]
Kapdi, Anant R. [1 ]
Gupta, Gaurav R. [1 ]
机构
[1] Inst Chem Technol, Dept Chem, Nathalal Parekh Marg Rd, Mumbai 400019, Maharashtra, India
[2] North Maharashtra Univ, Sch Chem Sci, Mumbai 425001, Maharashtra, India
关键词
Cetylpyridinium bromide; Heck coupling reaction; Heteroarylsubstituted stilbenes; Homogeneous catalysis; Surfactant ionic liquids; N-HETEROCYCLIC-CARBENE; TEMPERATURE IONIC LIQUIDS; C-H ALKENYLATION; AQUEOUS-SOLUTIONS; CETYLPYRIDINIUM BROMIDE; 2-SUBSTITUTED AZAARENES; DIRECT ELECTROCHEMISTRY; CATIONIC SURFACTANT; THERMAL-STABILITY; HEAT-CAPACITIES;
D O I
10.1002/slct.201904837
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The main objective of this study was to replace the traditionally applicable volatile organic solvents and imidazolium-based ionic liquid solvents with thermally stable surfactant, cetylpyridinium bromide as surfactant ionic liquid (SIL) and examine the potential of the same as viable reaction medium in the synthesis of stilbenes, quinoxaline and pyridone decorated substrates via Heck cross-coupling reaction. This work thoroughly investigates the thermal, spectral and morphological properties of cetylpyridinium bromide as surfactant ionic liquid. Cetylpyridinium bromide is a well-known germicide with well-established degradation mechanism and displays remarkable solvent properties for the homogeneously catalysed Heck cross-coupling reactions, which is of great significance to enlarge the applications window of cetylpyridinium bromide from biologically significant surfactant material to the choice of solvent in synthetic organic chemistry.
引用
收藏
页码:4251 / 4262
页数:12
相关论文
共 152 条
[1]   Anodic dissolution of metals in ionic liquids [J].
Abbott, Andrew P. ;
Frisch, Gero ;
Hartley, Jennifer ;
Karim, Wrya O. ;
Ryder, Karl S. .
PROGRESS IN NATURAL SCIENCE-MATERIALS INTERNATIONAL, 2015, 25 (06) :595-602
[2]   Processing of metals and metal oxides using ionic liquids [J].
Abbott, Andrew P. ;
Frisch, Gero ;
Hartley, Jennifer ;
Ryder, Karl S. .
GREEN CHEMISTRY, 2011, 13 (03) :471-481
[3]   Ionic Liquid-Carbon Nanomaterial Hybrids for Electrochemical Sensor Applications: a Review [J].
Abo-Hamad, Ali ;
AlSaadi, Mohammed AbdulHakim ;
Hayyan, Maan ;
Juneidi, Ibrahim ;
Hashim, Mohd Ali .
ELECTROCHIMICA ACTA, 2016, 193 :321-343
[4]   Vapor pressure of ionic liquids at low temperatures from AC-chip-calorimetry [J].
Ahrenberg, Mathias ;
Beck, Martin ;
Neise, Christin ;
Kessler, Olaf ;
Kragl, Udo ;
Verevkin, Sergey P. ;
Schick, Christoph .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2016, 18 (31) :21381-21390
[5]   Application of ionic liquids as recyclable green catalysts for selective alkylation of phenol [J].
Amirfirouzkouhi, Hamideh ;
Kharat, Ali Nemati .
SEPARATION AND PURIFICATION TECHNOLOGY, 2018, 196 :132-139
[6]  
[Anonymous], 2014, ENV FRIENDLY SYNTHES
[7]   Ionic liquids for the convenient synthesis of functional nanoparticles and other inorganic nanostructures [J].
Antonietti, M ;
Kuang, DB ;
Smarsly, B ;
Yong, Z .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (38) :4988-4992
[8]   Adsorptive Stripping Voltammetric Determination of Morin in Tea Infusions and Chocolate Drinks on a Gold Electrode. Effect of Cetylpyridinium Bromide on the Sensitivity of the Method [J].
Arancibia, Veronica ;
Gracia-Beltran, Olimpo ;
Hurtado, John ;
Nagles, Edgar .
INTERNATIONAL JOURNAL OF ELECTROCHEMICAL SCIENCE, 2017, 12 (10) :9408-9417
[9]   Heterogeneous catalysis in ionic liquids: The heck reaction of bromobenzene with styrene over palladium supported on mesoporous carbon [J].
Aslanov, L. A. ;
Valetskii, P. M. ;
Zakharov, V. N. ;
Kabachii, Yu. A. ;
Kochev, S. Yu. ;
Romanovskii, B. V. ;
Yatsenko, A. V. .
PETROLEUM CHEMISTRY, 2008, 48 (05) :360-365
[10]   Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes with Primary Alcohols [J].
Barman, Milan K. ;
Waiba, Satyadeep ;
Maji, Biplab .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (29) :9126-9130