基于纳米二氧化硅与MCM-41的两种多相钯催化剂的合成及其在Suzuki反应中的应用（英文）
|
摘要
含氮膦配体的钯配合物分别被负载于纳米二氧化硅和MCM-41表面。由此得到的两种新型多相钯催化剂SiO_2@PNPPdCl_2(1)和MCM-41@PNPPdCl_2(2)均通过SEM(EDX)、TEM(SAED)、XRD、FT-IR、ICP-MS和TGA等手段进行全面表征。微观结构表明,这两种纳米颗粒具有完全不同的结构,1为不规则球体,2具有蜂窝孔状结构。然后进一步研究了纳米粒子1和2在Suzuki偶联反应中以乙醇和水为溶剂的温和条件下的催化性能。研究显示两种催化剂均具有较好的基团耐受性,循环利用4次的平均产率分别为81%(1)和89%(2)。它们的催化性能也略有不同,催化剂1的催化速率高于2,催化剂2具有较好的循环利用性能。
Palladium compounds containing diphosphine ligand with N atom were immobilized on the surface of nano silica and MCM-41 respectively. The resulting two novel heterogeneous Pd catalysts SiO_2@ PNPPdCl_2( 1) and MCM-41@ PNPPdCl_2( 2) were fully characterized by SEM( EDX),TEM( SAED),XRD,FT-IR,ICP-Ms and TGA. Microstructure tests showed that the two kinds of nanoparticles have completely different structures,1 has an irregular sphere structure and 2 has a honeycomb structure. The catalytic performance of nanoparticles 1 and 2 under mild conditions with EtO H/H_2O( v/v = 3/2) as solvent in Suzuki coupling reaction was further studied. The two catalysts had good group tolerance,and their average yields in four cycles were 81%( 1) and 89%( 2) respectively.Their catalytic properties are also slightly different. The catalytic rate of catalyst 1 is much faster than that of 2,while catalyst 2 has better recycling performance.
Palladium compounds containing diphosphine ligand with N atom were immobilized on the surface of nano silica and MCM-41 respectively. The resulting two novel heterogeneous Pd catalysts SiO_2@ PNPPdCl_2( 1) and MCM-41@ PNPPdCl_2( 2) were fully characterized by SEM( EDX),TEM( SAED),XRD,FT-IR,ICP-Ms and TGA. Microstructure tests showed that the two kinds of nanoparticles have completely different structures,1 has an irregular sphere structure and 2 has a honeycomb structure. The catalytic performance of nanoparticles 1 and 2 under mild conditions with EtO H/H_2O( v/v = 3/2) as solvent in Suzuki coupling reaction was further studied. The two catalysts had good group tolerance,and their average yields in four cycles were 81%( 1) and 89%( 2) respectively.Their catalytic properties are also slightly different. The catalytic rate of catalyst 1 is much faster than that of 2,while catalyst 2 has better recycling performance.
引文
[1]R Jana,T P Pathak,M S Sigman.Chem.Rev.,2011,111(3):1417~1492.
[2]N Miyaura,A Suzuki.J.Am.Chem.Soc..1979,19:866~867.
[3]N Miyaura,A Suzuki.Chem.Rev.,1995,95(7):2457~2483.
[4]T Hayashi,M Konishi,Y Kobori et al.J.Am.Chem.Soc.,1984,106(1):158~163.
[5]N Miyaura,K Yamada,A Suzuki.Tetrahed.Lett.,1979,20(36):3437~3440.
[6]R S Coleman,X Lu,I Modolo.J.Am.Chem.Soc.,2007,129(13):3826~3827.
[7]D A Albisson,R B Bedford,P S Noelle et al.Chem.Commun.,1998,(19):2095~2096.
[8]A Tyagi,A Yamamoto,H Yoshida.Catal.Sci.Technol.,2018,8(23):6196~6203.
[9]D Silva,P Fernanda,J L Fiorio et al.Ind.Eng.Chem.Res.,2018,57(48):16209~16216.
[10]J W Zhang,K K Sun,D D Li et al.Appl.Catal.A.,2019,569:190~195.
[11]C R Gogoi,P K Gogoi.Chem.Asian J.,2018,30(10):2225~2230.
[12]G Marck,A Villiger,R Buchecker.Tetrahed.Lett.,1994,35(20):3277~3280.
[13]G W Kabalka.R W Pagni,C M Hair.Org.Lett.,1999,1(9):1423~1425.
[14]F Amoroso,S Colussi,A Del Zotto et al.J.Mol.Catal.A,2010,315(2):197~204.
[15]Z Chen,Z M Cui,F Niu et al.Chem.Commun.,2010,46(35):6524~6526.
[16]H Yang,X Han,G Li et al.Green Chem.,2009,11(8):1184~1193.
[17]L Artok,H Bulut.Tetrahed.Lett.,2004,45(20):3881~3884.
[18]F Durap,M Rakap,M Aydemir et al.Appl.Catal.A.,2010,382(2):339~344.
[19]K Okumura,T Tomiyama,S Okuda et al.J.Catal.,2010,273(2):156~166.
[20]S Schweizer,J-M Becht,C L Drian.Tetrahedron,2010,66(3):765~772.
[21]P Basak,P Ghosh.Synth.Commun.,2018,48(19):2584~2599.
[22]P Tegeder,M Freitag,K M Chepiga.Chem.Eur.J.,2018,24(70):18682~18688.
[23]C M Crudden,M Sattsh,R Lewis.J.Am.Chem.Soc.,2005,127:10045~10050.
[24]S Paul,J H Clark,D J Macquarrie.Green Chem.,2001,3:23~25.
[25]S Paul,J H Clark.Green Chem.,2003,5:635~638.
[26]M Trilia,R Pleixats,M W C Man et al.Adv.Synth.Catal.,2008,350:577~590.
[27]N Gürbüz,Izdemir,T Sekin et al.J.Inorg.Organomet.Polym.,2004,14(2):149~159.
[28]P A Alfonso,E H Jamal,M M Dolores et al.J.Catal.,2018,367:283~295.
[29]N Miyaura,A Suzuki.Chem.Commun.,1979,19:866~867.
[30]D W Old,J P Wolfe,S L Buchwald.J.Am.Chem.Soc.,1998,120(37):9722~9723.
[31]A Aranyos,D W Old,A Kiyomori et al.J.Am.Chem.Soc.,1999,121(18):4369~4378.
[32]J P Wolfe,R A Singer,B H Yang et al.J.Am.Chem.Soc.,1999,121(41):9550~9561.
[33]M Cao,Z X Wang,J Zhang et al.Inorg.Chim.Acta,2018,469:402~407.
[34]A L Balch,M M Olmstead,S P Rowley.Inorg.Chim.Acta,1990,168:255~264.
[35]M Nikoorazm,F Ghorbani,Z Erfani et al.Chin.J.Catal.,2017,38:1413~1422.
[36]G B Smith,G C Dezeny,D L Hughes et al.J.Org.Chem.,1994,59(26):8151~8156.
[37]J P Corbet,G Mignani.Chem.Rev.,2006,106(7):2651~2710.
[2]N Miyaura,A Suzuki.J.Am.Chem.Soc..1979,19:866~867.
[3]N Miyaura,A Suzuki.Chem.Rev.,1995,95(7):2457~2483.
[4]T Hayashi,M Konishi,Y Kobori et al.J.Am.Chem.Soc.,1984,106(1):158~163.
[5]N Miyaura,K Yamada,A Suzuki.Tetrahed.Lett.,1979,20(36):3437~3440.
[6]R S Coleman,X Lu,I Modolo.J.Am.Chem.Soc.,2007,129(13):3826~3827.
[7]D A Albisson,R B Bedford,P S Noelle et al.Chem.Commun.,1998,(19):2095~2096.
[8]A Tyagi,A Yamamoto,H Yoshida.Catal.Sci.Technol.,2018,8(23):6196~6203.
[9]D Silva,P Fernanda,J L Fiorio et al.Ind.Eng.Chem.Res.,2018,57(48):16209~16216.
[10]J W Zhang,K K Sun,D D Li et al.Appl.Catal.A.,2019,569:190~195.
[11]C R Gogoi,P K Gogoi.Chem.Asian J.,2018,30(10):2225~2230.
[12]G Marck,A Villiger,R Buchecker.Tetrahed.Lett.,1994,35(20):3277~3280.
[13]G W Kabalka.R W Pagni,C M Hair.Org.Lett.,1999,1(9):1423~1425.
[14]F Amoroso,S Colussi,A Del Zotto et al.J.Mol.Catal.A,2010,315(2):197~204.
[15]Z Chen,Z M Cui,F Niu et al.Chem.Commun.,2010,46(35):6524~6526.
[16]H Yang,X Han,G Li et al.Green Chem.,2009,11(8):1184~1193.
[17]L Artok,H Bulut.Tetrahed.Lett.,2004,45(20):3881~3884.
[18]F Durap,M Rakap,M Aydemir et al.Appl.Catal.A.,2010,382(2):339~344.
[19]K Okumura,T Tomiyama,S Okuda et al.J.Catal.,2010,273(2):156~166.
[20]S Schweizer,J-M Becht,C L Drian.Tetrahedron,2010,66(3):765~772.
[21]P Basak,P Ghosh.Synth.Commun.,2018,48(19):2584~2599.
[22]P Tegeder,M Freitag,K M Chepiga.Chem.Eur.J.,2018,24(70):18682~18688.
[23]C M Crudden,M Sattsh,R Lewis.J.Am.Chem.Soc.,2005,127:10045~10050.
[24]S Paul,J H Clark,D J Macquarrie.Green Chem.,2001,3:23~25.
[25]S Paul,J H Clark.Green Chem.,2003,5:635~638.
[26]M Trilia,R Pleixats,M W C Man et al.Adv.Synth.Catal.,2008,350:577~590.
[27]N Gürbüz,Izdemir,T Sekin et al.J.Inorg.Organomet.Polym.,2004,14(2):149~159.
[28]P A Alfonso,E H Jamal,M M Dolores et al.J.Catal.,2018,367:283~295.
[29]N Miyaura,A Suzuki.Chem.Commun.,1979,19:866~867.
[30]D W Old,J P Wolfe,S L Buchwald.J.Am.Chem.Soc.,1998,120(37):9722~9723.
[31]A Aranyos,D W Old,A Kiyomori et al.J.Am.Chem.Soc.,1999,121(18):4369~4378.
[32]J P Wolfe,R A Singer,B H Yang et al.J.Am.Chem.Soc.,1999,121(41):9550~9561.
[33]M Cao,Z X Wang,J Zhang et al.Inorg.Chim.Acta,2018,469:402~407.
[34]A L Balch,M M Olmstead,S P Rowley.Inorg.Chim.Acta,1990,168:255~264.
[35]M Nikoorazm,F Ghorbani,Z Erfani et al.Chin.J.Catal.,2017,38:1413~1422.
[36]G B Smith,G C Dezeny,D L Hughes et al.J.Org.Chem.,1994,59(26):8151~8156.
[37]J P Corbet,G Mignani.Chem.Rev.,2006,106(7):2651~2710.