Palladium-catalyzed reactions of acylzirconocene chloride with organic halides

Tetrahedron Letters

Volumn 39, Issue 34, 1998, Pages 6249-6252

  Hanzawa, Yuji ^a   Tabuchi, Nobuhito ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Complexes; Coupling reactions; Palladium and compounds; Zirconium and compounds

Indexed keywords

ACYLZIRCONOCENE CHLORIDE; HALIDE; PALLADIUM; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ACYLATION; ARTICLE; CATALYSIS; DERIVATIZATION; DRUG STABILITY; DRUG SYNTHESIS; NONHUMAN; REACTION ANALYSIS;

EID: 0032552217     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01287-8     Document Type: Article

References (12)

1. 1. a) Bertelo, C. A.; Schwartz, J. J. Am. Chem. Soc. 1975, 97, 228.
2. b) Schwartz, J.; Labinger, J. A. Angew. Chem. Int. Ed. Engl. 1976, 15, 333.
3. c) Labinger, J. A. "Comprehensive Organic Synthesis" B. M. Trost and I. Fleming, Eds.; Pergamon Press: Oxford, 1991; Vol. 8; pp 667. Takacs, J. M. "Comprehensive Organometallic Chemistry II; E. W. Abel, F. G. A. Stone and G. Wilkinson, Eds.; Pergamon Press: Oxford, 1995; Vol. 12; pp 39.
4. c) Labinger, J. A. "Comprehensive Organic Synthesis" B. M. Trost and I. Fleming, Eds.; Pergamon Press: Oxford, 1991; Vol. 8; pp 667. Takacs, J. M. "Comprehensive Organometallic Chemistry II; E. W. Abel, F. G. A. Stone and G. Wilkinson, Eds.; Pergamon Press: Oxford, 1995; Vol. 12; pp 39.
5. 2. Waymouth, R. M.; Santarsiero, B. D.; Coots, R. J.; Bronikowski, M. J.; Grubbs, R. H. J. Am. Chem. Soc. 1986, 108, 1427 and references cited therein.
6. 3. Harada, S.; Taguchi, T.; Tabuchi, N.; Narita, K.; Hanzawa, Y. Angew. Chem. Int. Ed. Engl. in press.
7. 4. It has been reported that the palladium-catalyzed reactions of an acyltin species with acid halide and allylic halide gave α-diketone and allylketone, respectively. a) Verlhac, J.; Chanson, E.; Jousseaume, B.; Quintard, J. Tetrahedron Lett. 1985, 26, 6075.
8. b) Kosugi, M.; Naka, H.; Harada, S.; Sano, H.; Migita, T. Chem. Lett. 1987, 1371.
9. 2 might suggest one possibility of the transmetalation process of an acylzirconocene derivative to an acylzinc species. Similar observation has been reported in the Pd-catalyzed reaction of vinylzirconocene chloride derivatives with vinyl halide by Negishi et al. Negishi, E.; Okukado, N.; King, A. O.; Van Horn, D. E.; Spiegel, B. I. J. Am. Chem. Soc. 1978, 100, 2254.
10. 6. Structures of new compounds were determined unambiguously by spectroscopic (1H-, 13C-NMR, IR, MS) and combustion analyses.
11. 2 (1 equiv) can also be used as a less efficient catalyst.
12. 8. Tsuji, J. "Palladium Reagents and Catalyst: Innovations in Organic Synthesis" John Wiley & Sons, 1995.