负载型联三吡啶钯催化剂的制备及在Suzuki-Miyaura偶联反应中的应用
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摘要
以4-(对羟基苯基)-2,2';6',2″-联三吡啶为配体,盐酸活化的硅胶为载体,制备了二氧化硅负载的钯催化剂SiO_2-tpy-Pd。120℃下,DMF为溶剂、K_2CO_3作为碱,四丁基溴化铵(TBAB)为相转移催化剂,负载型SiO_2-tpy-Pd催化剂用量为0.5 mol%,可有效促进芳基卤与芳硼酸的Suzuki-Miyaura偶联反应。该负载钯催化剂循环使用6次,催化活性无显著降低。
The SiO_2 supported terpyridine-palladium( SiO_2-tpy-Pd) catalyst was prepared by 4-( [2,2'; 6',2″-terpyridin]-4'-yl)phenol as ligand and silica gel as carrier.The Suzuki-Miyaura reaction of aryl halide with aryl boric acid can be effectively promoted under the reaction temperature of 120 ℃,DMF as solvent,K_2CO_3 as base,TBAB as phase transfer catalyst,supported catalyst loading 0. 5 mol%.The catalyst can be reused at least six times without distinct activity decrease.
The SiO_2 supported terpyridine-palladium( SiO_2-tpy-Pd) catalyst was prepared by 4-( [2,2'; 6',2″-terpyridin]-4'-yl)phenol as ligand and silica gel as carrier.The Suzuki-Miyaura reaction of aryl halide with aryl boric acid can be effectively promoted under the reaction temperature of 120 ℃,DMF as solvent,K_2CO_3 as base,TBAB as phase transfer catalyst,supported catalyst loading 0. 5 mol%.The catalyst can be reused at least six times without distinct activity decrease.
引文
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[2]TUCKER C E,DE VRIES J G.Homogeneous catalysis for the production of fine chemicals.Palladium-and nicklelcatalysed aromatic carbon-carbon bond formation[J].Top.Catal.,2002,19(1):111-118.
[3]HAN Fu-she.Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions:a remarkable advance from palladium to nickel catalysts[J].Chem.Soc.Rev.,2013,12:5 270-5 289.
[4]SHELDON R A,ARENDS I,HANEFELD U.Green chemistry and catalysis[M].Wenheim:Wiley-VCH,4thed,2007.
[5]MOLNAR A.Efficient,selective,and recyclable Palladium catalysts in carbon-carbon coupling reactions[J].Chem.Rev.,2011,111(3):2 251-2 320.
[6]TAHER A,LEE D J,LEE I M.Graphene-supported palladium complex:a highly efficient,robust and recyclable catalyst for the Suzuki-Miyaura cross-coupling of various aryl halides[J].Synlett,2016,27(16):2 333-2 338.
[7]VISHAL K,FAHLMAN B D,SASIDHAR B S,et al.Magnetic nanoparticle-supported N-heterocyclic carbene-palladium(Ⅱ):a convenient,efficient and recyclable catalyst for Suzuki-Miyaura cross-coupling reactions[J].Catal.Lett.,2017,147(4):900-918.
[8]WANG Hong-bo,HU Yu-lin,LI De-jiang.Facile and efficient Suzuki-Miyaura coupling reaction of aryl halides catalyzed by Pd2(dba)3in ionic liquid/supercritical carbon dioxide biphasic system[J].J.Mol.Liq.,2016,218:429-433.
[9]YILMAZ B N,BARAN T,MENTE A.Fabrication and application of cellulose Schiff base supported Pd(Ⅱ)catalyst for fast and simple synthesis of biaryls via Suzuki coupling reaction[J].Appl.Catal.A:General,2017,531:36-44.
[10]苑嗣纯,王惠川,陈海波.联三吡啶配体及其衍生物合成进展[J].有机化学,2009,29(4):504-516.
[11]YOO D W,YOO S K,KIM C,et al.A novel mononuclear Fe(Ⅲ)mono(terpyridine)complex having labile solvent ligands and its catalytic activity[J].J.Chem.Soc.Dalton Trans.,2002,21:3 931-3 932.