Allylation of aldehydes via Umpolung of π-allylpalladium(II) with triethylborane

Tetrahedron Letters

Volumn 40, Issue 37, 1999, Pages 6795-6798

  Kimura, Masanari ^a   Kiyama, Iku ^a   Tomizawa, Tatsuya ^a   Horino, Yoshikazu ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Aldehydes; Allylation; Boron; Boron compounds; Palladium; Palladium compounds

Indexed keywords

ALDEHYDE; ALLYL COMPOUND; BENZOIC ACID DERIVATIVE; BORON; BORON DERIVATIVE; DIPHENYL ETHER DERIVATIVE; ETHER DERIVATIVE; PALLADIUM; PALLADIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS;

EID: 0033543756     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01359-3     Document Type: Article

References (16)

1. (a) Kimura, M.; Ogawa, Y.; Shimizu, M.; Sueishi, M.; Tanaka, S.; Tamaru, Y. Tetrahedron Lett. 1998, 39, 6903-6906.
2. (b) Shimizu, M.; Kimura, M.; Tanaka, S.; Tamaru, Y. ibid. 1998, 39, 609-612.
3. (c) Tamaru, Y.; Goto, S.; Tanaka, A.; Shimizu, M.; Kimura, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 878-880.
4. (d) Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. ibid. 1995, 34, 787-789.
5. For a review of a variety of Umpolung methods of Π-allylpalladium(II), see: Tamaru, Y. J. Organometal. Chem. 1999, 576, 215-231.
6. (a) Kimura, M.; Fujimatsu, H.; Ezoe, A.; Shibata, K.; Shimizu, M.; Matsumoto, S.; Tamaru, Y. Angew. Chem., Int. Ed. Engl. 1999, 38, 397-400.
7. (b) Kimura, M.; Ezoe, A.; Shibata, K.; Tamaru, Y. J. Am. Chem. Soc. 1998, 120, 4033-4034.
8. Aryl group transfer from arylboranes to various types of palladium(II) intermediates has been well documented: (a) Miyaura, N. Synthesis of biaryls via the cross-coupling reaction of arylboronic acids, In Advances in Metal-Organic Chemistry; JAI: London, 1998; Vol. 6, pp. 187-243.
9. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483. In contrast to this, examples of alkyl group transfer from alkylboranes to palladium(II) intermediates are scarce; alkyl group transfer to acylpalladium(II):
10. (c) Ishiyama, T.; Murata, M.; Suzuki, A.; Miyaura, N. J. Chem. Soc., Chem. Commun. 1995, 295-296.
11. (d) Ishiyama, T.; Oh-e, T.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1992, 33, 4465-4468 and references cited therein. Alkyl group transfer to arylpalladium(II):
12. (e) Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J.; Tang, M.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 2845-2847.
13. (f) Kojima, A.; Honzawa, S.; Boden, C. D. J.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 3455-3458 and references cited therein.
14. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293.
15. (b) Brown, H. C.; Racherla, U. S.; Pellechia, P. J. J. Org. Chem. 1990, 55, 1868-1874.
16. 4) and concentrated in vacuo and the residue is purified by column chromatography over silica gel hexane-ethyl acetate 16/1, v/v) to provide 2a in 68% yield.