Selective reaction of π-allyl(alkyloxy)palladium(II) complexes toward β-decarbopalladation, β-dehydropalladation, and reductive elimination

Tetrahedron Letters

Volumn 39, Issue 46, 1998, Pages 8475-8478

  Harayama, Hiroto ^a   Kimura, Masanari ^a   Tanaka, Shuji ^a   Tamara, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKADIENE; CYCLOALKANE; PALLADIUM; PARAFORMALDEHYDE;

CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DATA ANALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SYNTHESIS;

EID: 0032511948     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01865-6     Document Type: Article

References (14)

1. (1) (a) Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424-4431, and references therein.
2. (2) (a) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335-5336.
3. (b) Crowe, W.E.; Rachita, M. J. ibid. 1995, 117, 6787-6788.
4. (3) (a)Sato, Y.; Saito, N.; Mori, M. Tetrahedron Lett. 1997, 38, 3931-3934.
5. (b)Sato, Y.; Takimoto, M.; Mori, M. ibid, 1996, 37, 887-890, and references therein.
6. (4) (a) Okamoto, S.; Iwakubo, M.; Kobayashi, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 6984-6990.
7. (b) Lee, J.; Ha J. D.; Cha, J. K. ibid, 1997, 119, 8127-8128, and references therein.
8. (5) Harayama, H.; Kuroki, T.; Kimura, M.; Tanaka, S.; Tamaru, Y. Angew. Chem. Int. Ed. Engl. 1997, 36, 2352-2354.
9. (6) Although not being correct for some derivatives, for simplicity, the 1,3-dioxacyclohexan-2-one and 1,3-dioxane systems are numbered uniformly as indicated in equation 4.
10. (7) The selective hydrogen delivery at C3 (not at the allylically related C5, providing 3-pentenyl formates) suggests an intermediacy of σ-allyl(hydrido)palladium(II) species III, stabilized by an intramolecular formyl group coordination to the palladium(II) metal.
11. (8) Insertion of formaldehyde into Ni-O bonds: Han, R.; Hillhouse, G. L. J. Am. Chem. Soc, 1997, 119, 8135-8136.
12. (9) (a) Murahashi, S.-I.; Naota, T.; Ito, K.; Maeda, Y.; Taki, H. J. Org. Chem. 1987, 52, 4319-4327.
13. (b)Tamaru, Y.; Yamada, Y.; Inoue, K.; Yamamoto, Y.; Yoshida, Z. ibid. 1983, 48, 1286-1292.
14. (10) For example, 4,8-dimetbyl-1,3,7-nonatriene was obtained in less than 3% isolated yield by the reaction of 6-methyl-5-hepten-2-one and allyltriphenylphosphonium bromide (tert-BuOK, THF or n-BuLi, ether). The triene was prepared in 61% yield according to Yamamoto's modification: Ikeda, Y.; Ukai, J.; Ikeda, N.; Yamamoto, H. Tetrahedron 1987, 43, 723-730.