Recyclable and eco-friendly Pd-complexed graphene oxide/N-heterocyclic carbene catalyst for various coupling reactions in aqueous phase

被引：41

作者：

Kim, Seongsoo ^{[1
]}

Cho, Hong-Jun ^{[2
]}

Shin, Dong-Sik ^{[3
]}

Lee, Sang-Myung ^{[1
]}

机构：

[1] Kangwon Natl Univ, Dept Chem Engn, Chuncheon Si 24341, Gangwon Do, South Korea

[2] Seoul Natl Univ, Sch Chem & Biol Engn, Seoul 08826, South Korea

[3] Sookmyung Womens Univ, Dept Chem & Biol Engn, Seoul 04310, South Korea

来源：

TETRAHEDRON LETTERS | 2017年 / 58卷 / 25期

基金：

新加坡国家研究基金会;

关键词：

Heterogeneous catalyst; Graphene oxide; N-Heterocyclic carbene; Palladium; C-C cross coupling; SUZUKI-MIYAURA; PALLADIUM COMPLEX; GRAPHITE OXIDE; MIZOROKI-HECK; SONOGASHIRA; NANOPARTICLES; CHLORIDES; EFFICIENT;

D O I：

10.1016/j.tetlet.2017.05.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, we report recyclable Pd-complexed graphene oxide (GO) catalysts with a bulky N-heterocyclic carbene (NHC) ligand (GO/NHC-Pd) for various cross-coupling reactions in the aqueous phase. To prepare GO/NHC-Pd, the NHC precursor and a trimethoxy-silane linker were combined on the GO surface via condensation, followed by the Pd chelation over GO/NHC. The GO-based catalysts were applied to three types of C-C cross-coupling reactions including Suzuki, Heck and Sonogashira reactions in the aqueous phase, to evaluate their catalytic performance. The reusability of the catalysts was tested by performing five consequent cross-coupling reactions. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：2421 / 2425

页数：5

共 28 条

[1] Weakly ligated palladium complexes PdCl2(RCN)2 in piperidine:: versatile catalysts for Sonogashira reaction of vinyl chlorides at room temperature [J].

Alami, M ;

Crousse, B ;

Ferri, F .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 624 (1-2) :114-123

[2]

Crisp GT, 1998, CHEM SOC REV, V27, P427

[3] N-Heterocyclic carbene (NHC) ligands and palladium in homogeneous cross-coupling catalysis: a perfect union [J].

Fortman, George C. ;

Nolan, Steven P. .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5151-5169

[4] Probing the Thermal Deoxygenation of Graphene Oxide Using High-Resolution In Situ X-ray-Based Spectroscopies [J].

Ganguly, Abhijit ;

Sharma, Surbhi ;

Papakonstantinou, Pagona ;

Hamilton, Jeremy .

JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (34) :17009-17019

[5] A Merrifield resin supported Pd-NHC complex with a spacer(Pd-NHC@SP-PS) for the Sonogashira coupling reaction under copper- and solvent-free conditions [J].

Jadhav, Sanjay N. ;

Kumbhar, Arjun S. ;

Mali, Sawanta S. ;

Hong, Chang Kook ;

Salunkhe, Rajashri S. .

NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) :2333-2341

[6] Pulicaria glutinosa plant extract: a green and eco-friendly reducing agent for the preparation of highly reduced graphene oxide [J].

Khan, Mujeeb ;

Al-Marri, Abdulhadi H. ;

Khan, Merajuddin ;

Mohri, Nils ;

Adil, Syed Farooq ;

Al-Warthan, Abdulrahman ;

Siddiqui, Mohammed Rafiq H. ;

Alkhathlan, Hamad Z. ;

Berger, Ruediger ;

Tremel, Wolfgang ;

Tahir, Muhammad Nawaz .

RSC ADVANCES, 2014, 4 (46) :24119-24125

[7] Using silane-functionalized graphene oxides for enhancing the interfacial bonding strength of carbon/epoxy composites [J].

Lee, Chang Yeong ;

Bae, Ji-Hun ;

Kim, Tae-Yoon ;

Chang, Seung-Hwan ;

Kim, Soo Young .

COMPOSITES PART A-APPLIED SCIENCE AND MANUFACTURING, 2015, 75 :11-17

[8] Synthesis and Characterization of Graphene and Graphene Oxide Based Palladium Nanocomposites and Their Catalytic Applications in Carbon-Carbon Cross-Coupling Reactions [J].

Lee, Minjae ;

Kim, Bo-Hyun ;

Lee, Yuna ;

Kim, Beom-Tae ;

Park, Joon B. .

BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (07) :1979-1984

[9] Selective and efficient platinum(0)-carbene complexes as hydrosilylation catalysts [J].

Markó, IE ;

Stérin, S ;

Buisine, O ;

Mignani, G ;

Branlard, P ;

Tinant, B ;

Declercq, JP .

SCIENCE, 2002, 298 (5591) :204-206

[10] Probing the potential of N-heterocyclic carbenes in molecular electronics:: redox-active metal centers interlinked by a rigid ditopic carbene ligand [J].

Mercs, Laszlo ;

Neels, Antonia ;

Albrecht, Martin .

DALTON TRANSACTIONS, 2008, (41) :5570-5576

← 1 2 3 →