Copper catalyzed Grignard cross-coupling reaction with β-perfluoroalkyl-substituted alkyl halides

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5557-5560

  Shimizu, Rie ^a   Yoneda, Eiichi ^a   Fuchikami, Takamasa ^a  

^a SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PERFLUORO COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0030605820     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01155-0     Document Type: Article

References (12)

1. 1. Urata, H.; Kosukegawa, O.; Ishii, Y.; Yugari, H.; Fuchikami, T. Tetrahedron Lett., 1989, 30, 4403-4406.
2. 2. Urata, H.; Ishii, Y.; Fuchikami, T. Tetrahedron Lett., 1989, 30, 4407-4410.
3. 3. Urata, H.; Maekawa, H.; Takahashi, S.; Fuchikami, T. J. Org. Chem., 1991, 56, 4320-4322.
4. 6
5. 5. Numamoto, S.; Kawakami, Y.; Yamashita, Y. Bull. Chem. Soc. Jpn., 1981, 54, 2831-2832.
6. 6. Tsuji, J.; Kaito, M.; Takahashi, T. Bull. Chem. Soc. Jpn., 1978, 51, 547-549.
7. 9
8. 8. Castle, P. L.; Widdowson, D. A. Tetrahedron Lett., 1986, 27, 6013-6016.
9. 9. Yuan, K.; Scott, W. J. Tetrahedron Lett., 1989, 30, 4779-4782.
10. 10. Satisfactory analytical and spectral data were obtained for all new compounds.
11. 11. Fuchikami, T.; Ojima, I. Tetrahedron Lett., 1984, 25, 303-306.
12. 12. In the cases of the reactions of iodide 1 with alkyl Grignard reagents having β-hydrogen(s), halogenmetal exchange reaction between 1 and Grignard reagents is an inevitable side reaction. Thus, the treatment of iodide 1 with octylmagnesium chloride (1.1 equiv.) in THF at r.t. for 1 h without copper catalyst, followed by the treatment with an excess of benzaldehyde, resulted in the formation of 3-perfluorooctyl-1-phenylpropanol (17) in 40 % yield with little recovered 1. However, the same treatment of 1 with 2-methyl-2-phenylpropylmagnesium chloride gave 17 in only 8% yield, in addition to more than 70% of unchanged 1. (formula presented)