The Pd(0) and Pd(II) SBA-TU-anchored catalysts in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions: A comparative catalytic study

被引:8
作者
Beiranvand, Masoumeh [1 ]
Habibi, Davood [1 ]
机构
[1] Bu Ali Sina Univ, Fac Chem, Dept Organ Chem, Hamadan, Iran
关键词
SBA-15; Tetra-urea ligand; Mizoroki-Heck; Suzuki-Miyaura; Cross-coupling; SUPRAMOLECULAR POLYMER; MESOPOROUS SILICA; CONJUGATED DIENES; EFFICIENT; NANOREACTOR; DIAMINATION; DERIVATIVES; OXIDATION; COMPLEX; GREEN;
D O I
10.1016/j.molstruc.2022.134174
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 surface of the mesoporous silica SBA-15 (SBA) was modified by a tetra-urea (TU) ligand (SBA@TU), and the palladium ions were anchored within the multidentate pore channels (SBA@TU@Pd(II)) and re-duced by NaBH4 (SBA@TU@Pd(0)). Then, the nano-structure reduced catalyst was characterized by FT-IR, EDX, elemental mapping analysis, XRD, SEM, TEM, TGA/DTA/DCS, and BET analysis. After that, the catalytic activity of the SBA@TU @Pd(0) catalyst was successfully studied in the Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions under mild reaction conditions for preparation of 1(a-l) and 2(a-i), respectively in short reaction times and high yields. Also, the Mizoroki-Heck and Suzuki-Miyaura cross-coupling re-actions were performed by the non-reduced nano-catalyst (SBA@TU@Pd(II)) under similar reaction con-ditions. The reaction yields were the same for both catalysts, but the reaction time was different which was shorter (30 min) for SBA@TU@Pd(0), while for SBA@TU@Pd(II) the reaction times were increased to about 80 and 70 min, respectively.(c) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数:15
相关论文
共 52 条
[1]   Efficient imidazolium salts for palladium-catalyzed Mizoroki-Heck and Suzuki-Miyaura cross-coupling reactions [J].
Amini, Mojtaba ;
Bagherzadeh, Mojtaba ;
Rostamnia, Sadegh .
CHINESE CHEMICAL LETTERS, 2013, 24 (05) :433-436
[2]   Applications of biological urea-based catalysts in chemical processes [J].
Atashkar, Bahareh ;
Zolfigol, Mohammad Ali ;
Mallakpour, Shadpour .
MOLECULAR CATALYSIS, 2018, 452 :192-246
[3]   A Bis (BICAAC) Palladium(II) Complex: Synthesis and Implementation as Catalyst in Heck-Mizoroki and Suzuki-Miyaura Cross Coupling Reactions [J].
Chakrabortty, Soumyadeep ;
Kaur, Mandeep ;
Adhikari, Manu ;
Manar, Krishna K. ;
Singh, Sanjay .
INORGANIC CHEMISTRY, 2021, 60 (09) :6209-6217
[4]   Ring-selective functionalization of N,N′-diarylureas by regioselective N-alkylation and directed ortho metalation [J].
Clayden, J ;
Turner, H ;
Pickworth, M ;
Adler, T .
ORGANIC LETTERS, 2005, 7 (15) :3147-3150
[5]   Lateral lithiation of N,N′-diaryl ureas [J].
Clayden, Jonathan ;
Dufour, Jeremy .
TETRAHEDRON LETTERS, 2006, 47 (39) :6945-6946
[6]   THE C-H BOND-ENERGY OF BENZENE [J].
DAVICO, GE ;
BIERBAUM, VM ;
DEPUY, CH ;
ELLISON, GB ;
SQUIRES, RR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (09) :2590-2599
[7]   Hierarchical macroporous-mesoporous SBA-15 sulfonic acid catalysts for biodiesel synthesis [J].
Dhainaut, Jeremy ;
Dacquin, Jean-Philippe ;
Lee, Adam F. ;
Wilson, Karen .
GREEN CHEMISTRY, 2010, 12 (02) :296-303
[8]   Three-Dimensional Printing in Catalysis: Combining 3D Heterogeneous Copper and Palladium Catalysts for Multicatalytic Multicomponent Reactions [J].
Diaz-Marta, Antonio S. ;
Tubio, Carmen R. ;
Carbajales, Carlos ;
Fernandez, Carmen ;
Escalante, Luz ;
Sotelo, Eddy ;
Guitian, Francisco ;
Laura Barrio, V. ;
Gil, Alvaro ;
Coelho, Alberto .
ACS CATALYSIS, 2018, 8 (01) :392-404
[9]   Tuning the Viscoelastic Properties of Bis(urea)-Based Supramolecular Polymer Solutions by Adding Cosolutes [J].
Francisco, Kelly Roberta ;
Dreiss, Cecile A. ;
Bouteiller, Laurent ;
Sabadini, Edvaldo .
LANGMUIR, 2012, 28 (41) :14531-14539
[10]   Copper(II) Schiff-Base Complex Modified UiO-66-NH2(Zr) Metal-Organic Framework Catalysts for Knoevenagel Condensation-Michael Addition-Cyclization Reactions [J].
Ghobakhloo, Farzaneh ;
Azarifar, Davood ;
Mohammadi, Masoud ;
Keypour, Hassan ;
Zeynali, Hamid .
INORGANIC CHEMISTRY, 2022, 61 (12) :4825-4841