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

Abstract

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.

Highly efficient recyclable polymer anchored palladium catalyst for CC and CN coupling reactions

“…The most readily available form of supported catalyst is palladium on charcoal, which is widely used for heterogeneous hydrogenation and also has a growing importance in carbon-carbon bond-forming reactions [30][31][32]. There are many examples of heterogeneous catalysts for C C coupling reactions, and they are prepared by different approaches like encapsulation or immobilization of a catalytically active metal complex on solid supports such as zeolites [33][34][35], covalent grafting of such active complexes onto reactive polymer surfaces [36][37][38] or inorganic porous matrices [39,40], and ordered mesoporous silica such as MCM-41 [41][42][43].…”

Activity and Recyclability Improvement Through Adjusting the Tethering Strategy for Pd-Catalyzed Suzuki–Miyaura Coupling Reaction of Aryl Chlorides

“…Several materials such as silica [33][34][35], polymers [36][37][38][39][40] have been developed for the immobilization of NHCPd catalysts. Jin's group reported a silica gel supported NHC-Pd catalyst in 2008 [33].…”

Suzuki–Miyaura coupling under air in water promoted by polymer supported palladium nanoparticles

“…Usually, this crosscoupling reaction is catalyzed by soluble phosphane palladium complexes in organic solvents but such a protocol suffers from the difficulty in recovering and reusing the expensive homogeneous catalysts. To overcome this drawback, much work has been devoted to the development of reusable Pd heterogeneous catalysts [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19]. In this regard, recyclable nanocatalysts [20][21][22][23][24][25][26][27][28] experienced great prosperity in the past decade, because they combine high surface area with excellent accessibility of the reactants to the active sites.…”