Preparation, characterization and application of silica-supported palladium complex as a new and heterogeneous catalyst for Suzuki and Sonogashira reactions

被引:65
作者
Ghiaci, Mehran [1 ]
Zarghani, Monireh [1 ]
Moeinpour, Farid [2 ]
Khojastehnezhad, Amir [3 ]
机构
[1] Isfahan Univ Technol, Dept Chem, Esfahan 8415683111, Iran
[2] Islamic Azad Univ, Dept Chem, Coll Sci, Bandar Abbas Branch, Bandar Abbas, Iran
[3] Islamic Azad Univ, Dept Chem, Coll Sci, Mashhad Branch, Mashhad, Iran
关键词
Pd nanoparticles; silica-bonded; Suzuki; Sonogashira; cross-coupling reactions; MIYAURA COUPLING REACTION; RECYCLABLE CATALYST; IONIC-LIQUID; EFFICIENT CATALYST; REUSABLE CATALYST; NANOPARTICLES; HECK; OXIDATION; SBA-15; WATER;
D O I
10.1002/aoc.3165
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
An efficient heterogeneous Pd catalytic system has been developed, based on immobilization of Pd nanoparticles (PNPs) on a silica-bonded propylamine-cyanuric-cysteine (SiO2-pA-Cyan-Cys) substrate. The synthesized catalyst was characterized by transmission electron microscopy, scanning electron microscopy, FT-IR, N-2 adsorption analysis (BET), TGA and inductively coupled plasma/atomic emission spectroscopy, and catalytic activity of this catalyst was investigated in the Suzuki and Sonogashira cross-coupling reactions. The catalysts showed excellent performance in these two reactions, including various aryl halide derivatives (except aryl chloride derivatives) with phenylboronic acid and phenylacetylene under green conditions. Moreover, the catalyst was recycled for several runs without any significant loss of catalytic activity. Copyright (C) 2014 John Wiley & Sons, Ltd.
引用
收藏
页码:589 / 594
页数:6
相关论文
共 42 条
[1]   Silica-supported terpyridine palladium(II) complex as an efficient and reusable catalyst for Heck and Suzuki cross-coupling reactions [J].
Amini, Mostafa M. ;
Feiz, Afsaneh ;
Dabiri, Minoo ;
Bazgir, Ayoob .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (02) :86-90
[2]   Highly efficient solvent free oxidation of ethylbenzene using some recyclable catalysts: The role of linker in competency of manganese nanocatalysts [J].
Arshadi, Mohammad ;
Ghiaci, Mehran .
APPLIED CATALYSIS A-GENERAL, 2011, 399 (1-2) :75-86
[3]   Copper-free Sonogashira coupling reactions catalyzed by a water-soluble Pd-salen complex under aerobic conditions [J].
Bakherad, Mohammad ;
Keivanloo, Ali ;
Bahramian, Bahram ;
Hashemi, Mahdieh .
TETRAHEDRON LETTERS, 2009, 50 (14) :1557-1559
[4]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[5]   Silica supported palladium-phosphine complex: recyclable catalyst for Suzuki-Miyaura cross-coupling reactions at ambient temperature [J].
Chen, Wei ;
Li, Pinhua ;
Wang, Lei .
TETRAHEDRON, 2011, 67 (02) :318-325
[6]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[7]   Acetanilide palladacycle: an efficient catalyst for room- temperature Suzuki- Miyaura crosscoupling reaction [J].
Dewan, Anindita ;
Buragohain, Zenith ;
Mondal, Manoj ;
Sarmah, Gayatri ;
Borah, Geetika ;
Bora, Utpal .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (04) :230-233
[8]   Efficient clay supported Pd nanoparticles as heterogeneous catalyst for arylation of alkenes [J].
Ghiaci, Mehran ;
Ansari, Fatemeh ;
Sadeghi, Zahra ;
Gil, A. .
CATALYSIS COMMUNICATIONS, 2012, 21 :82-85
[9]   Metalloporphyrin covalently bound to silica. Preparation, characterization and catalytic activity in oxidation of ethyl benzene [J].
Ghiaci, Mehran ;
Molaie, Fatemeh ;
Sedaghat, Mohammad E. ;
Dorostkar, Nasim .
CATALYSIS COMMUNICATIONS, 2010, 11 (08) :694-699
[10]   Active palladium catalyst supported by bulky diimine ligand catalyzed Suzuki- Miyaura coupling reaction in water under phosphanefree and low catalyst loading conditions + [J].
Gholinejad, Mohammad ;
Karimkhani, Vahid ;
Kim, Il .
APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (04) :221-224