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8248182 
Journal Article 
Catalytic Homogeneous Hydrogenation of Arenes. 6.1 Reaction Scope for the η3-C3H5Co[P(OCH3)3]3 Catalyst 
Stuhl, LS; Hirsekorn, MRDFJ; Bleeke, JR; Stevens, AE; Muetterties, EL 
1978 
Yes 
Journal of the American Chemical Society
ISSN: 0002-7863
EISSN: 1520-5126 
100 
8 
2405-2410 
English 
The scope and selectivity of η3-C3H5Co[P(OCH3)3]3 as a catalyst precursor for the homogeneous hydrogenation of arenes at room temperature and low pressure (1-3 atm) have been examined for a variety of substituted benzenes and polycyclic aromatic and heterocyclic compounds. Pronounced stereoselectivity for the cis addition of H2 and the formation of cis ring junctions has been observed. For example, benzene +D2 gave>95% all cis C6H6D6, naphthalene +H2 gave cis-decalin with no detectable trans isomer, and anthracene + H2 gave>95% of the cis-syn-cis-perhydroanthracene. The scope of the reaction is reasonably large. Catalytic hydrogenation was demonstrated for benzenes with substitutent groups that include -R, -OR, -COOR, -COR, -CH⎓CHR, -C≡CR, and -NR2. The catalyst system is subject to steric inhibition by ring substituents on the arene ring. Electron-withdrawing and nucleophilic substituents such as halogen, -NO2, and -CN also inhibit the reaction. The selectivity for arene vs. olefin hydrogenation in competitive systems is discussed. Comparisons are drawn with metal surface catalyzed hydrogenation. © 1978, American Chemical Society. All rights reserved.