Reusable Immobilized Iron(II) Nanoparticle Precatalysts for Ligand-Free Kumada Coupling

被引:8
作者
Akiyama, Toshiki [1 ]
Wada, Yuki [1 ]
Jenkinson, Kellie [2 ]
Honma, Tetsuo [3 ]
Tsuruta, Kazuki [3 ]
Tamenori, Yusuke [3 ]
Haneoka, Hitoshi [4 ]
Takehara, Tsunayoshi [4 ]
Suzuki, Takeyuki [4 ]
Murai, Kenichi [1 ]
Fujioka, Hiromichi [1 ]
Sato, Yoshihiro [5 ]
Wheatley, Andrew E. H. [2 ]
Arisawa, Mitsuhiro [1 ]
机构
[1] Osaka Univ, Grad Sch Pharmaceut Sci, Yamada Oka 1-6, Suita, Osaka 5650871, Japan
[2] Univ Cambridge, Dept Chem, Lensfield Rd, Cambridge CB2 1EW, England
[3] Japan Synchrotron Radiat Res Inst, 1-1-1 Kouto, Sayo, Hyogo 6795198, Japan
[4] Osaka Univ, Inst Sci & Ind Res, Ibaraki, Osaka 5670047, Japan
[5] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Kuta 12,Nishi 6, Sapporo, Hokkaido 0600812, Japan
基金
英国工程与自然科学研究理事会;
关键词
iron; nanoparticle; precatalyst; reusable catalyst; Kumada coupling; ligand-free; ALKYL-HALIDES; GRIGNARD-REAGENTS; CATALYZED KUMADA; BOND FORMATION; ARYL GRIGNARDS; ACTIVATION; ARYLATION; CHLORIDES; BIARYL; INHIBITORS;
D O I
10.1021/acsanm.8b01742
中图分类号
TB3 [工程材料学];
学科分类号
0805 ; 080502 ;
摘要
A nanoparticle (NP)-based precatalyst has been developed for organic synthesis: sulfur-modified Au-supported Fe (SAFe). The SAFe was easily prepared through a three-step procedure involving simultaneous in situ metal NP and nanospace organization (PSSO). This method avoids the need for preformed templates for immobilizing and stabilizing the metal nanoparticles. On account of the relative safety and enormous earth abundance of iron, SAFe potentially represents an ideal precatalyst for carbon-carbon bond-forming cross-coupling reactions. As such, it has been applied as a precatalyst to Kumada coupling under ligand-free conditions, proving to be capable of being recycled and used repeatedly for this reaction. Analysis of SAFe and of reaction mixtures suggested that the active species in these reactions are produced in situ by assemblies of iron-based NPs.
引用
收藏
页码:6950 / 6958
页数:17
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