7126-64-9Relevant articles and documents
Water-medium C-H activation over a hydrophobic perfluoroalkane-decorated metal-organic framework platform
Huang, Yuan-Biao,Shen, Min,Wang, Xusheng,Huang, Ping,Chen, Ruiping,Lin, Zu-Jin,Cao, Rong
, p. 1 - 7 (2015/11/24)
The use of water as reaction medium in the heterogeneous activation of C-H bonds has numerous advantages in terms of environmental benign, safety and cost efficiency impact. However, it is severely hampered because the reactants are difficult to dissolve in water and contact with the active sites of heterogeneous catalysts. Herein, we choose perfluoroalkane-functionalized mesoporous metal-organic framework (MOF) NU-1000 as a hydrophobic platform to encapsulate ultrafine palladium nanoparticles (Pd NPs) for C-H activation in water. The resultant Pd NPs stabilized by the perfluoroalkane exhibited high activity and regioselectivity in the direct C-H arylation of indoles in water. The introduction of perfluoroalkane chains into the mesoporous pores of NU-1000 provides hydrophobic surfaces to facilitate access of the reactants to the active sites to guarantee the high activity.
One-pot approach to 1,2-disubstituted indoles via Cu(II)-catalyzed coupling/cyclization under aerobic conditions and its application for the synthesis of polycyclic indoles
Gao, Jilong,Shao, Yingying,Zhu, Jiaoyan,Zhu, Jiaqi,Mao, Hui,Wang, Xiaoxia,Lv, Xin
, p. 9000 - 9008 (2014/12/11)
A straightforward assembly of 1,2-disubstituted indoles has been developed through a Cu(II)-catalyzed domino coupling/cyclization process. Under aerobic conditions, a wide range of 1,2-disubstituted indole derivatives were efficiently and facilely synthesized from 2-alkynylanilines and boronic acids. 2-(2-Bromoaryl)-1-aryl-1H-indoles, which were selectively generated in one pot under the Cu catalysis, afforded the indolo[1,2-f]phenanthridines via Pd-catalyzed intramolecular direct C(sp2)-H arylation. The one-pot tandem approaches to the polycyclic indole derivatives were also successfully achieved.
Palladium nanoparticles encapsulated in a metal-organic framework as efficient heterogeneous catalysts for direct C2 arylation of indoles
Huang, Yuanbiao,Lin, Zujin,Cao, Rong
scheme or table, p. 12706 - 12712 (2011/12/04)
Highly dispersed palladium nanoparticles (Pd NPs) encapsulated in the mesoporous cages of the metal-organic framework (MOF) MIL-101(Cr) have been prepared by using the wetness impregnation method. The Pd NPs were characterized by powder X-ray diffraction (PXRD), N2 adsorption, transmission electron microscopy, inductively coupled plasma atomic emission spectroscopy (ICP-AES), and X-ray photoelectron spectroscopy (XPS). The particles size ((2.6 ± 0.5) nm) of the obtained Pd NPs was in good agreement with the cage diameters (2.9 and 3.4 nm) of the MOF. The resulting Pd/MIL-101(Cr) catalyst exhibited extremely high catalytic activities in the direct C2 arylation of substituted indoles by using only 0.1 mol-% of the Pd catalyst. Moreover, the catalyst is easily recoverable and can be reused several times without leaching into solution and loss of activity. The combination of the highly dispersible Pd NPs within the accessible mesoporous cages and the favorable adsorption of the aryl halides on MIL-101 are suspected to be the main reasons for the observed high activities of the Pd/MIL-101(Cr) catalyst in the direct C2 arylation of indoles. MOF-encapsulated catalyst: Highly dispersed palladium nanoparticles encapsulated in the mesoporous metal-organic framework (MOF) MIL-101(Cr) exhibited high catalytic activities for the direct C2 arylation of substituted indoles with a range of substituted iodobenzenes (see figure) by only using a very low amount of the Pd catalyst (0.1 mol-%). The catalyst is easily recovered and can be reused several times without leaching into solution and loss of activity.