Facile route to dihydroindacene type ligands using multiple Heck reactions on aryl polybromides

Tetrahedron Letters

Volumn 43, Issue 47, 2002, Pages 8475-8478

  Ceccon, Alberto ^a   Crociani, Laura ^a,b   Santi, Saverio ^a   Venzo, Alfonso ^b   Biffis, Andrea ^a   Boccaletti, Giovanni ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b CNR   (Italy)

Author keywords

Catalysis; Functionalized benzenes; Heck reaction; Ligand molecules; Palladium

Indexed keywords

ACRYLIC ACID BUTYL ESTER; ALKENE DERIVATIVE; BROMINE DERIVATIVE; LIGAND; METAL COMPLEX; PALLADIUM COMPLEX;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CHEMICAL BOND; CYCLIZATION; HECK REACTION; ISOMER; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037131708     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02087-7     Document Type: Article

References (17)

1. . For a comprehensive review, see: Beletskaya I.P., Cheprakov A.V. Chem. Rev. 100:2000;3009.
2. Biffis A., Zecca M., Basato M. J. Mol. Catal. A: Chem. 173:2001;249.
3. De Vries J.G. Can. J. Chem. 79:2001;1086.
4. . For some examples, see: de Meijere A., Meier F.E. Angew. Chem., Int. Ed. Engl. 33:1994;2379.
5. Santi S., Ceccon A., Bisello A., Crociani L., Gambaro A., Tiso M., Venzo A. Organometallics. 21:2002;2679.
6. Ceccon A., Bisello A., Crociani L., Gambaro A., Ganis P., Manoli F., Santi S., Venzo A. J. Organomet. Chem. 600:2000;94.
7. Ceccon A., Bisello A., Gambaro A., Ganis P., Manoli F., Santi S., Venzo A. J. Organomet. Chem. 594:2000;315.
8. Wightman H., Wain R.J., Lake D.H. Can. J. Chem. 1971;1360.
9. Corruthers W., Stewart H.N.M., Hansell P.G., Kelly K.M. J. Chem. Soc. 1967;2607.
10. Stapler J.T., Bornstein J. J. Heterocyclic Chem. 10:1973;983.
11. Bell W.L., Curtis C.J., Eigenbrot C.W. Jr., Pierpont C.G., Robbins J.L., Smart J.C. Organometallics. 6:1987;266.
12. Trogen L., Edlund U. Acta Chem. Scand. B33:1979;109.
13. Dabrouch M.R., Jara P., Mendez L., Portilla Y., Abril D., Alfonso G., Chavez I., Manriquez J.M. Organometallics. 20:2001;5591.
14. 4, filtered and evaporated under reduced pressure. The oily residue was chromatographed over silica gel (eluent petroleum ether) to afford the diester as a white oil. In the case of the dibromide ar-3 the residue was a solid from which the diester was recovered pure as a white solid by washing the residue with methanol. All the yields are reported in Table 1 .
15. Littke A.F., Fu G.C. J. Org. Chem. 64:1999;10.
16. 6: C, 65.45; H, 5.49. Found: C, 65.21; H, 5.20%.
17. Basato M., Grassi A., Valle G. Organometallics. 14:1995;4439.