On-Water and Efficient Ullmann-Type O-Arylation Cross Coupling Reaction of Phenols and Aryl Tosylates in the Presence of Fe3O4@Starch-Au as Nanocatalyst

被引：19

作者：

Mousavi-Mashhadi, Seyed Ali ^{[1
]}

Shiri, Ali ^{[1
]}

机构：

[1] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, Mashhad, Razavi Khorasan, Iran

来源：

CHEMISTRYSELECT | 2021年 / 6卷 / 16期

关键词：

C-O Cross Coupling; Green Chemistry; Heterogeneous Catalysis; Nano Fe3O4 Starch; Ullmann-Type Diaryl Ether Synthesis; GREEN SYNTHESIS; GRAPHENE OXIDE; NANOPARTICLES; CATALYST; PD; HALIDES; ACTIVATION;

D O I：

10.1002/slct.202004327

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Gold complex-functionalized magnetic core-shell nanoparticles (Fe3O4@Starch-Au) were prepared by hydrothermal method and characterized by Fourier transform-infrared (FT-IR), X-ray diffraction (XRD), thermo gravimetric (TGA), vibrating sample magnetometer (VSM), scanning electron microscopy (SEM), transmission electron microscopy (TEM), inductively coupled plasma (ICP), and energy-dispersive X-ray (EDX) analyses. The activity of the new synthesized catalyst was employed in cross-coupling reactions of nontoxic aryl tosylates with phenols to provide the desired diaryl ethers through Ullmann-type diaryl synthesis. The coupling of several aryltosylates and phenols including aromatic and heterocyclic ones are allowed to perform on water in remarkable yields. This work provides a facile, green, and environmentally friendly method, which is employed to present a precious catalyst that can be recovered six times.

引用

页码：3941 / 3951

页数：11

共 63 条

[1]

[Anonymous], 2010, ANGEW CHEM, V122, P5360

[2]

[Anonymous], 2006, ANGEW CHEM, V118, P4427

[3]

[Anonymous], 2006, ANGEW CHEM, V118, P8064

[4]

Armisén R, 2009, WOODHEAD PUBL FOOD S, P82, DOI 10.1533/9781845695873.82

[5] Pd/PTABS: Low Temperature Etherification of Chloroheteroarenes [J].

Bhilare, Shatrughn ;

Bandaru, Siva Sankar Murthy ;

Shah, Jagrut ;

Chrysochos, Nicolas ;

Schulzke, Carola ;

Sanghvi, Yogesh S. ;

Kapdi, Anant R. .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (21) :13088-13102

[6] Synthesis of nonsymmetrically N,N′-diaryi-substituted 4,4′-bipyridinium salts with redox-tunable and titanium dioxide (TiO2)-anchoring properties [J].

Bongard, D ;

Möller, M ;

Rao, SN ;

Corr, D ;

Walder, L .

HELVETICA CHIMICA ACTA, 2005, 88 (12) :3200-3209

[7] Palladium nanoparticles on polysaccharide-derived mesoporous materials and their catalytic performance in C-C coupling reactions [J].

Budarin, Vitaly L. ;

Clark, James H. ;

Luque, Rafael ;

Macquarrie, Duncan J. ;

White, Robin J. .

GREEN CHEMISTRY, 2008, 10 (04) :382-387

[8] Significantly improved method for the Pd-catalyzed coupling of phenols with aryl halides: Understanding ligand effects [J].

Burgos, Carlos H. ;

Barder, Timothy E. ;

Huang, Xiaohua ;

Buchwald, Stephen L. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) :4321-4326

[9] Inhibitory effect of obovatol on nitric oxide production and activation of NF-κB/MAP kinases in lipopolysaccharide-treated RAW 264.7 cells [J].

Choi, Myoung Suk ;

Lee, Seung Ho ;

Cho, Ho Seong ;

Kim, Youngsoo ;

Yun, Yeo Pyo ;

Jung, Hai Young ;

Jung, Jae Kyoung ;

Lee, Bum Chun ;

Pyo, Hyeong Bae ;

Hong, Jin Tae .

EUROPEAN JOURNAL OF PHARMACOLOGY, 2007, 556 (1-3) :181-189

[10] A general and mild Ullmann-type synthesis of diaryl ethers [J].

Cristau, HJ ;

Cellier, PP ;

Hamada, S ;

Spindler, JF ;

Taillefer, M .

ORGANIC LETTERS, 2004, 6 (06) :913-916

← 1 2 3 4 5 6 7 →