Pd black deposited on polypropylene sheet as a highly selective catalyst for hydrogenation of alkenes

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3717-3721

  Maki, Shojiro ^a   Okawa, Makiko ^a   Makii, Toshimichi ^a   Hirano, Takashi ^a   Niwa, Haruki ^a  

^a UNIVERSITY OF ELECTRO COMMUNICATIONS   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; PALLADIUM; POLYPROPYLENE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL REACTION; HYDROGENATION; HYDROGENOLYSIS; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037471456     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00551-3     Document Type: Article

References (21)

1. Newham J. Chem. Rev. 63:1963;123.
2. Fletcher H.G. Methods Carbohydr. Chem. II:1963;166.
3. Bindra J.S., Grodski A. J. Org. Chem. 43:1978;3240.
4. House H.O. Modern Synthetic Reactions. 1972;23-26 W. A. Benjamin, Inc.
5. Sajiki H., Hattori K., Hirota K. J. Org. Chem. 63:1998;7990-7992.
6. Sajiki H., Hirota K. Tetrahedron. 54:1998;13981-13996.
7. Maki S., Harada Y., Hirano T., Niwa H., Yoshida Y., Ogata S., Nakamatsu S., Inoue H., Iwakura C. Synth. Commun. 30:2000;3575-3583.
8. 3M Propore™ (Sumitomo 3M, Ltd). It is also good for the deposition and reaction to use Tyvek® (polyethylene).
9. After simply removing the Pd catalyst with forceps and concentrating the reaction solvent without carrying out any purification, the generation rate and the structure of all the reaction products were confirmed by directly measuring the residue using NMR and comparing this to the NMR data of the standard samples synthesized by alternative routes. Moreover, additional experiments were also carried out for all the reactions in order to confirm the reproducibility.
10. 3 298.1569.
11. 3 300.1725.
12. 3 210.1256.
13. Other protonic solvents, for example EtOH and i-PrOH, gave results similar to those with MeOH.
14. 4 298.1205.
15. 4 300.1362.
16. 4 210.0892.
17. 4 208.0736.
18. 13C NMR).
19. The reactivity of the Pd black-(G) in nitrobenzene and cyanobenzene was examined (Scheme). Nitrobenzene was satisfactorily reduced and quantitatively converted into aniline in 8 h in methanol under atmospheric pressure at room temperature. Cyanobenzene was reduced to the corresponding benzyl amine without producing a by-product though the reaction was very slow under atmospheric pressure and required 18 days to complete.
20. Maki S., Okawa M., Matsui R., Hirano T., Niwa H. Synlett. 2001;1590-1592.
21. It was confirmed that 1 was converted into 2 in quantitative yield within 1 h by employing Pd black-(G) which had been continuously used as a hydrogenation catalyst for 1000 h.