Platinum-Catalyzed Facile Arene Hydrogenation: Dramatic Effect of Activated Carbon and Vinylsiloxane Derivatives on the Catalyst Efficiency

被引:2
作者
Motoyama, Yukihiro [1 ,2 ]
Ohnishi, Kenta [1 ]
Shibuya, Hayato [1 ]
Joshi, Prerna [1 ]
Yoshimura, Masamichi [1 ,2 ]
机构
[1] Toyota Technol Inst, Dept Adv Sci & Technol, Nagoya 4688511, Japan
[2] Toyota Technol Inst, Res Ctr Smart Energy Technol, Nagoya 4688511, Japan
关键词
Arenes; Carbon; Catalyst design; Hydrogenation; Platinum; CHEMOSELECTIVE HYDROGENATION; AROMATIC INTERACTIONS; PD; 1,1'-BINAPHTHYLS; NANOPARTICLES; NITROARENES; REDUCTION; REMOVAL;
D O I
10.1002/ajoc.202200666
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Combination of Karstedt's catalyst or Pt(dba)(2) [dba: dibenzylideneacetone] with activated carbon was found to be an efficient catalyst system for the arene hydrogenation of a variety of functionalized aromatic compounds. The reaction proceeds at ambient temperature under atmospheric hydrogen pressure to afford the corresponding carbo- and heterocyclic compounds in good to high yields without contamination of the metallic species. The addition of activated carbon in the reaction mixture was proved to be crucial for not only sustaining the catalytic activity but also trapping the platinum species effectively after the reaction. Similar sustaining effect was observed by the addition of vinyl siloxane derivatives.
引用
收藏
页数:5
相关论文
共 41 条
[1]   Reductions of aromatic amino acids and derivatives [J].
Ager, DJ ;
Prakash, I .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (02) :164-167
[2]  
[Anonymous], GUIDELINE ELEMENTAL
[3]  
[Anonymous], 2019, ANGEW CHEM, V131, P10570
[4]  
[Anonymous], 2002, IMPLEMENTING GUIDELI
[5]   Partially hydrogenated 1,1′-binaphthyl as ligand scaffold in metal-catalyzed asymmetric synthesis [J].
Au-Yeung, TTL ;
Chan, SS ;
Chan, ASC .
ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (05) :537-555
[6]   Polysiloxane-Pd nanocomposites as recyclable chemoselective hydrogenation catalysts [J].
Chauhan, BPS ;
Rathore, JS ;
Bandoo, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (27) :8493-8500
[7]   Synthesis of polysiloxane stabilized palladium colloids and evidence of their participation in silaesterification reactions [J].
Chauhan, BPS ;
Rathore, JS ;
Chauhan, M ;
Krawicz, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (10) :2876-2877
[8]   The absence of favorable aromatic interactions between β-sheet peptides [J].
Chung, D ;
Dou, YM ;
Baldi, P ;
Nowick, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9998-9999
[9]   Chemical routes for the transformation of biomass into chemicals [J].
Corma, Avelino ;
Iborra, Sara ;
Velty, Alexandra .
CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502
[10]   HOST-GUEST COMPLEXATION .8. MACROCYCLIC POLYETHERS SHAPED BY 2 RIGID SUBSTITUTED DINAPHTHYL OR DITETRALYL UNITS [J].
CRAM, DJ ;
HELGESON, RC ;
PEACOCK, SC ;
KAPLAN, LJ ;
DOMEIER, LA ;
MOREAU, P ;
KOGA, K ;
MAYER, JM ;
CHAO, Y ;
SIEGEL, MG ;
HOFFMAN, DH ;
SOGAH, GDY .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (10) :1930-1946