The utilization of supercritical carbon dioxide in the palladium- catalyzed hydroarylation of β-substituted-α,β-enones

Synlett

Volumn , Issue 5, 2000, Pages 650-652

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Gasparrini, Francesco ^a   Pace, Paola ^a   Villani, Claudio ^b  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

^b UNIVERSITY OF CHIETI   (Italy)

Author keywords

Catalysis; Hydroarylation; Palladium; Supercritical carbon dioxide

Indexed keywords

CARBON DIOXIDE; IODIDE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATION; NONHUMAN; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034074623     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (22)

1. Jessop, P.G.; Leitner, W. Chemical Synthesis Using Supercritical Fluids Wiley-VCH, Weinheim 1999.
2. 2 in catalytic reactions with transition metal complexes, see: Baiker, A. Chem. Rev. 1999, 99, 453; Jessop, P.G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Darr, J.A.; Poliakoff, M. Chem. Rev. 1999, 99, 495.
3. 2 in catalytic reactions with transition metal complexes, see: Baiker, A. Chem. Rev. 1999, 99, 453; Jessop, P.G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Darr, J.A.; Poliakoff, M. Chem. Rev. 1999, 99, 495.
4. 2 in catalytic reactions with transition metal complexes, see: Baiker, A. Chem. Rev. 1999, 99, 453; Jessop, P.G.; Ikariya, T.; Noyori, R. Chem. Rev. 1999, 99, 475; Darr, J.A.; Poliakoff, M. Chem. Rev. 1999, 99, 495.
5. Koch, D.; Leitner, W. J. Am. Chem. Soc. 1998, 120, 13398.
6. 2 in palladium-catalyzed reactions, see: a) Kayaki, Y.; Noguchi, Y:, Iwasa, S.; Ikariya, T.; Noyori, R. Chem. Commun. 1999, 1235;
7. b) Cacchi, S.; Fabrizi, G.; Gasparrini, F.; Villani, C. Synlett 1999, 345;
8. c) Bhanage, B.M.; Ikushima, Y.; Shirai, M.; Arai, M. Tetrahedron Lett. 1999, 40, 6427;
9. d) Shezad, N.; Oakes, R.S.; Clifford, A.A.; Rayner, C.M. Tetrahedron Lett. 1999, 40, 2221;
10. e) M.A. Carrol; A.B. Holmes Chem. Commun. 1998, 1395;
11. f) D.K. Morita; D.R. Pesiri; S.A. David; W.H. Glaze; W. Tumas Chem. Commun. 1998, 1397.
12. For some examples of reduction of σ-alkylpalladium adducts by triethylamine to give hydroarylation products in conventional organic solvents, see: Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047; Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813; Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
13. For some examples of reduction of σ-alkylpalladium adducts by triethylamine to give hydroarylation products in conventional organic solvents, see: Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047; Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813; Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
14. For some examples of reduction of σ-alkylpalladium adducts by triethylamine to give hydroarylation products in conventional organic solvents, see: Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047; Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813; Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
15. For some examples of reduction of σ-alkylpalladium adducts by triethylamine to give hydroarylation products in conventional organic solvents, see: Friestad, G.K.; Branchaud, B.P. Tetrahedron Lett. 1995, 36, 7047; Stokker, G.E. Tetrahedron Lett. 1987, 28, 3179; Amorese, A.; Arcadi, A.; Bernocchi, E.; Cacchi, S.; Cerrini, S.; Fedeli, W.; Ortar, G. Tetrahedron 1989, 45, 813; Cacchi, S.; Arcadi, A. J. Org. Chem. 1983, 48, 4236.
16. 2: C 83.52; H 6.37; Found C 83.46; H 6.35.
17. Arcadi, A.; Bernocchi, E.; Cacchi, S.; Marinelli, F.; Ortar, G. J. Organomet. Chem. 1989, 368, 249 and the references cited therein.
18. The reaction of butenone with phenyl iodide under our conditions (40 h) produced the corresponding hydroarylation and vinylic substitution products in 56 and 18% yield, respectively.
19. Formation of the vinylic substitution derivative from cyclohex-2-en-1-one is likely to involve the intermediacy of a palladium(II) enolate complex: Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494; Ito, Y.; Hirao, T.; A.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
20. Formation of the vinylic substitution derivative from cyclohex-2-en-1-one is likely to involve the intermediacy of a palladium(II) enolate complex: Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494; Ito, Y.; Hirao, T.; A.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
21. 11 the electron-withdrawing power of the carbonyl group of 5,6-dihydro-2H-pyran-2-one is expected to be higher than that of cyclohexanone.
22. Bordwell, F.G. Acc. Chem. Res. 1988, 21, 456.