Efficient semihydrogenation of the C-C triple bond using palladium on pumice as catalyst

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2857-2858

  Gruttadauria, Michelangelo ^a   Noto, Renato ^a,b   Deganello, Giulio ^b,c   Liotta, Leonarda F ^b  

^a Dipartimento di Chimica Organica E Paterno   (Italy)

^b CNR   (Italy)

^c Dipartimento di Chimica Fisica   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM;

ADSORPTION; ARTICLE; CATALYST; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; REACTION TIME; STEREOCHEMISTRY;

EID: 0033515715     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00311-1     Document Type: Article

References (10)

1. Rylander, P. N. Hydrogenation Methods; Academic Press: London, 1985.
2. (a) Rylander, P. N. Catalytic Hydrogenation in Organic Synthesis; Academic Press: New York, 1979;
3. (b) Henrick, C. A. Tetrahedron 1977, 33, 1845-1889.
4. Arista, L.; Gruttadauria, M.; Noto, R. Heterocycles, 1998, 48, 1325-1330.
5. The catalyst was prepared by us following a procedure derived from Yermakov; Yermakov, Yu. I. Catalysis Rev. 1986, 13, 77-120. See also: Fagherazzi, G.; Benedetti, A.; Duca, D.; Martorana, A.; Deganello, G.; J. Catal. 1994, 150, 117-126.
6. The catalyst was prepared by us following a procedure derived from Yermakov; Yermakov, Yu. I. Catalysis Rev. 1986, 13, 77-120. See also: Fagherazzi, G.; Benedetti, A.; Duca, D.; Martorana, A.; Deganello, G.; J. Catal. 1994, 150, 117-126.
7. Typical procedure: Compounds 1 (0.46 mmol) in absolute ethanol (20 mL) were stirred with Pd/pumice (30 mg) or Pd/C (9 mg) or Lindlar's catalyst (18 mg) for the time indicated in the table. The reactions were performed in a three necked glass reactor with jacket. The reactor was connected to a line operating at a constant atmospheric pressure of H2 by using the first two necks. The last neck, closed by a silicone septum, allowed withdrawing of samples for HPLC analysis. The suspension was magnetically stirred.The constant temperature (25.0±0.1°C) was ensured by a thermostat.
8. trans-homoallylic alcohols were not detected by HPLC analysis.
9. Venezia, A. M.; Rossi, A.; Duca, D.; Martorana, A.; Deganello, G. Appl. Catal., A, 1995, 125, 113-128.
10. Deganello, G.; Duca, D.; Liotta, L. F.; Martorana, A.; Venezia, A. M. Gazz. Chim. It., 1994, 124, 229-239.