Copper-Incorporated Porous Polydivinylbenzene as Efficient and Recyclable Heterogeneous Catalyst in Ullmann Biaryl Ether Coupling.

Wang, Liang; Zhang, Jian; Sun, Jing; Zhu, LongfENg; Zhang, Haiyan; Liu, Fujian; ZhENg, Dafang; MENg, Xiangju; Shi, Xiaodong; Xiao, FENg ‐ Shou

The preparation of efficient and stable heterogeneous catalyst is very important for organic transformations. Herein, we report a copper-incorporated porous, Schiff base-modified polydivinylbenzene (PDVB-SB-Cu) as an excellent heterogeneous catalyst in promoting Ullmann biaryl ether coupling reactions. PDVB-SB-Cu was synthesized by incorporating copper species into PDVB-SB. Combined characterizations by using 13C NMR, IR, XPS, N2 adsorption, and TEM indicated the synthesis of copper-Schiff base species on porous PDVB. Catalytic tests in the Ullmann biaryl ether coupling of iodobenzene and phenol indicated that the PDVB-SB-Cu catalyst gave high activity similar to that of the homogeneous Schiff base-stabilized copper catalyst. This good reactivity was likely due to the polymer-based porous materials, which provided more effective interactions between substrates and catalytic centers. Importantly, PDVB-SB-Cu has extraordinary recyclability. The advantages of high activities and good recyclability made the PDVB-SB-Cu catalyst a new class of solid-support transition metal catalysts for fine chemical preparation.

CATALYSTS; IODOBENZENE; COUPLING reactions (Chemistry); ADSORPTION (Chemistry); COPPER catalysts

ChemCatChem, 2013, Vol 5, Issue 6, p1606

1867-3880

Academic Journal

10.1002/cctc.201200578