3,4,5-Trifluorobenzeneboronic acid as an extremely active amidation catalyst

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4196-4197

  Ishihara, Kazuaki ^a   Ohara, Suguru ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001094491     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9606564     Document Type: Article

References (17)

1. For a review of the synthesis of amides and related compounds, see: Benz, G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: New York, 1991; Vol. 6, Chapter 2.3.
2. 3: (d) Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569.
3. 3: (d) Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569.
4. 3: (d) Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569.
5. 3: (d) Ishihara, K.; Kuroki, Y.; Hanaki, N.; Ohara, S.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 1569.
6. (a) Pelter, A.; Levitt, T. E.; Nelson, P. Tetrahedron 1970, 26, 1539.
7. (b) Trapani, G.; Reho, A.; Latrofa, A. Synthesis 1983, 1013.
8. (c) Tani, J.; Oine, T.; Inoue, I. Synthesis 1975, 714.
9. (d) Collum, D. B.; Chen, S.-C.; Ganem, B. J. Org. Chem. 1978, 43, 4393.
10. We were unable to prepare aliphatic perfluoroalkylboronic acids.
11. Boronic acid 1 was prepared by addition of trimethyl borate to Grignard reagent, which was generated in situ from 3,4,5-trifluorobromobenzene and magnesium (turnings) in THF.
12. We previously used 2 as an efficient Lewis acid catalyst; see: (a) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
13. We previously used 2 as an efficient Lewis acid catalyst; see: (a) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
14. We previously used 2 as an efficient Lewis acid catalyst; see: (a) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490. (b) Ishihara, K.; Maruyama, T.; Mouri, M.; Gao, Q.; Furuta, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1993, 66, 3483. (c) Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.
15. 8) δ 4.02-4.08 (br, 0.24H, OH (for monomer)), 7.82 (s, 0.12H, p-H (for monomer)), 8.01 (s, 0.24H, o-H (for monomer)), 8.03 (s, 0.88H, p-H (for trimer)), 8.48 (s, 1.76H, o-H (for trimer)).
16. 2B), 7.96 (s, 1H, p-H), 8.51 (s, 2H, o-H).
17. This study was supported in part by the Yamada Science Foundation.