Nitrogen-rich porous covalent imine network (CIN) material as an efficient catalytic support for C-C coupling reactions

被引:118
作者
Bhunia, Manas K. [1 ]
Das, Swapan K. [1 ]
Pachfule, Pradip [2 ]
Banerjee, Rahul [2 ]
Bhaumik, Asim [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Mat Sci, Kolkata 700032, India
[2] Natl Chem Lab, Phys & Mat Chem Div, Pune 411008, Maharashtra, India
关键词
PALLADIUM NANOPARTICLES; MICROPOROUS POLYMER; RECYCLABLE CATALYSTS; NANOPOROUS POLYMER; HECK; SILICA; REUSABILITY; FRAMEWORKS; COMPLEXES;
D O I
10.1039/c1dt11350j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
In an effort to expand the realm of possibilities of nitrogen-rich porous materials that could be used in catalysis, herein we report the synthesis of a new highly nitrogen rich (ca. 45%) porous covalent imine network (CIN-1) material employing simple Schiff base chemistry and further grafting its surface with palladium. Pd-loaded CIN-1 support acts as a truly heterogeneous catalyst towards Suzuki C-C coupling reaction between aryl halides with arylboronic acids. High surface area and excellent accessibility of the catalytic sites make it very efficient for heterogeneous catalysis. The stability of the catalyst due to intimate contact between nitrogen-rich organic support and metal allows several reuses with only a minor loss in catalytic activity.
引用
收藏
页码:1304 / 1311
页数:8
相关论文
共 58 条
[1]   N-doped carbon nanotubes for liquid-phase C=C bond hydrogenation [J].
Amadou, Julien ;
Chizari, Kambiz ;
Houlle, Matthieu ;
Janowska, Izabela ;
Ersen, Ovidiu ;
Begin, Dominique ;
Pham-Huu, Cuong .
CATALYSIS TODAY, 2008, 138 (1-2) :62-68
[2]   Silica-supported imine palladacycles - recyclable catalysts for the Suzuki reaction? [J].
Bedford, RB ;
Cazin, CSJ ;
Hursthouse, MB ;
Light, ME ;
Pike, KJ ;
Wimperis, S .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 633 (1-2) :173-181
[3]   Thermoregulated liquid/liquid catalyst separation and recycling [J].
Behr, Arno ;
Henze, Guido ;
Schomaecker, Reinhard .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (12-13) :1485-1495
[4]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[5]   Remarkably facile Heck and Suzuki reactions in water using a simple cationic surfactant and ligand-free palladium catalysts [J].
Bhattacharya, S ;
Srivastava, A ;
Sengupta, S .
TETRAHEDRON LETTERS, 2005, 46 (20) :3557-3560
[6]   Covalent Triazine Framework as Catalytic Support for Liquid Phase Reaction [J].
Chan-Thaw, Carine E. ;
Villa, Alberto ;
Katekomol, Phisan ;
Su, Dangsheng ;
Thomas, Arne ;
Prati, Laura .
NANO LETTERS, 2010, 10 (02) :537-541
[7]   Functionalized mesoporous cross-linked polymer as efficient host for loading gold nanoparticles and its electrocatalytic behavior for reduction of H2O2 [J].
Chandra, Debraj ;
Jena, Bikash Kumar ;
Raj, C. Retna ;
Bhaumik, Asim .
CHEMISTRY OF MATERIALS, 2007, 19 (25) :6290-6296
[8]   Shape-dependent catalytic activity of copper oxide-supported Pd(0) nanoparticles for Suzuki and cyanation reactions [J].
Chattopadhyay, Kalicharan ;
Dey, Raju ;
Ranu, Brindaban C. .
TETRAHEDRON LETTERS, 2009, 50 (26) :3164-3167
[9]   High Catalytic Activity of Palladium(II)-Exchanged Mesoporous Sodalite and NaA Zeolite for Bulky Aryl Coupling Reactions: Reusability under Aerobic Conditions [J].
Choi, Minkee ;
Lee, Dong-Hwan ;
Na, Kyungsu ;
Yu, Byung-Woo ;
Ryoo, Ryong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (20) :3673-3676
[10]   ON MECHANISM OF SCHIFF BASE FORMATION AND HYDROLYSIS [J].
CORDES, EH ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :832-&