Mechanistic studies of the Suzuki-Miyaura reaction with aryl bromides using Pd supported on micro- and mesoporous activated carbons

被引:27
作者
Kurokhtina, Anna A. [1 ]
Larina, Elizaveta V. [1 ]
Schmidt, Alexander F. [1 ]
Malaika, Anna [2 ]
Krzyzynska, Beata [2 ]
Rechnia, Paulina [2 ]
Kozlowski, Mieczyslaw [2 ]
机构
[1] Irkutsk State Univ, Dept Chem, Irkutsk 664003, Russia
[2] Adam Mickiewicz Univ, Fac Chem, PL-61614 Poznan, Poland
基金
俄罗斯基础研究基金会;
关键词
Suzuki-Miyaura reaction; Reaction mechanism; Heterogeneous catalysis; Selectivity; Palladium; CROSS-COUPLING REACTIONS; LIGAND-FREE SUZUKI; PALLADIUM NANOPARTICLES; HECK REACTIONS; HETEROGENEOUS MECHANISMS; MIZOROKI-HECK; IN-SITU; CATALYSTS; COMPLEXES; CHLORIDES;
D O I
10.1016/j.molcata.2013.08.032
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 Suzuki-Miyaura reaction has been studied using palladium supported on modified activated carbons as catalysts. Two kinds of supports (micro- and mesoporous) have been prepared from plum stones and oak wood, and subsequently modified with different agents (HNO3, (NH4)(2)S2O8, air or ammonia) in order to produce new or alter the existing surface functional groups. The selectivity changes in the competitive Suzuki-Miyaura reaction indicate a substantial contribution of the heterogeneous catalysis to the reaction mechanism. Thus, the data obtained are not consistent with the widely accepted point of exclusive homogeneous catalysis of the Suzuki-Miyaura reaction. (C) 2013 Elsevier B.V. All rights reserved.
引用
收藏
页码:327 / 332
页数:6
相关论文
共 53 条
[1]   Studies on the catalytic ability of palladium wire, foil and sponge in the Suzuki-Miyaura cross-coupling [J].
Amoroso, Francesco ;
Cersosimo, Ulma ;
Del Zotto, Alessandro .
INORGANICA CHIMICA ACTA, 2011, 375 (01) :256-262
[2]   Toward the Ideal Catalyst: From Atomic Centers to a "Cocktail" of Catalysts [J].
Ananikov, Valentine P. ;
Beletskaya, Irina P. .
ORGANOMETALLICS, 2012, 31 (05) :1595-1604
[3]   Heterogeneous or homogeneous? A case study involving palladium-containing perovskites in the Suzuki reaction [J].
Andrews, SP ;
Stepan, AF ;
Tanaka, H ;
Ley, SV ;
Smith, MD .
ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (05) :647-654
[4]   Orthopalladated phosphinite complexes as high-activity catalysts for the Suzuki reaction [J].
Bedford, RB ;
Hazelwood, SL ;
Horton, PN ;
Hursthouse, MB .
DALTON TRANSACTIONS, 2003, (21) :4164-4174
[5]   Efficient and recyclable catalyst of palladium nanoparticles stabilized by polymer micelles soluble in water for Suzuki-Miyaura reaction, Ostwald ripening process with palladium nanoparticles [J].
Beletskaya, Irina P. ;
Kashin, Alexander N. ;
Khotina, Irina A. ;
Khokhlov, Alexey R. .
SYNLETT, 2008, (10) :1547-1552
[6]  
Böhm VPW, 2001, CHEM-EUR J, V7, P4191
[7]   Pd nanoparticles embedded in sponge-like porous silica as a Suzuki-Miyaura catalyst: Similarities and differences with homogeneous catalysts [J].
Budroni, Gerolamo ;
Corma, Avelino ;
Garia, Hermenegildo ;
Primo, Ana .
JOURNAL OF CATALYSIS, 2007, 251 (02) :345-353
[8]   PEPPSI-Type Palladium Complexes Containing Basic 1,2,3-Triazolylidene Ligands and Their Role in Suzuki-Miyaura Catalysis [J].
Canseco-Gonzalez, Daniel ;
Gniewek, Andrzej ;
Szulmanowicz, Michal ;
Mueller-Bunz, Helge ;
Trzeciak, Anna M. ;
Albrecht, Martin .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (19) :6055-6062
[9]   Pd-leaching and Pd-removal in Pd/C-catalyzed Suzuki couplings [J].
Chen, Jeng-Shiou ;
Vasiliev, Aleksey N. ;
Panarello, Anthony P. ;
Khinast, Johannes G. .
APPLIED CATALYSIS A-GENERAL, 2007, 325 (01) :76-86
[10]   Suzuki-Miyaura cross-coupling with quasi-heterogeneous palladium [J].
Conlon, DA ;
Pipik, B ;
Ferdinand, S ;
LeBlond, CR ;
Sowa, JR ;
Izzo, B ;
Collins, P ;
Ho, GJ ;
Williams, JM ;
Shi, YJ ;
Sun, YK .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (08) :931-935