Bis(pentafluorophenyl)borinic Acid as a Highly Effective Oppenauer Oxidation Catalyst for Allylic and Benzylic Alcohols

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 5664-5665

  Ishihara, Kazuaki ^a   Kurihara, Hideki ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000273878     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970959d     Document Type: Article

References (16)

1. Oppenauer, R. V. Rec. Trav. Chim. Pays-Bas 1937, 56, 137.
2. Reviews, see: (a) Djerassi, C. Org. React. 1951, 6, 207. (b) de Graauw, C. F.; Peters, J. A.; van Bekkum, H.; Huskens, J. Synthesis 1994, 1007.
3. Reviews, see: (a) Djerassi, C. Org. React. 1951, 6, 207. (b) de Graauw, C. F.; Peters, J. A.; van Bekkum, H.; Huskens, J. Synthesis 1994, 1007.
4. 2 (2 mol %, 130 °C), see: Ishii, Y.; Nakano, T.; Inada, A.; Kishigami, Y.; Sakurai, K.; Ogawa, M. J. Org. Chem. 1986, 51, 240.
5. 4 (20 mol %, 20 °C), see: Krohn, K.; Knauer, B.; Küpke, J.; Seebach, D.; Beck, A. K.; Hayakawa, M. Synthesis 1996, 1341.
6. Fatiadi, A. J. Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; p 119.
7. For the selective dehydration of anti aldols to α,β-enones catalyzed by 1, see: Ishihara, K.; Kurihara, H.; Yamamoto, H. Synlett 1997, 597.
8. (a) Chambers, R. D.; Chivers, T. J. Chem. Soc. 1964, 4782.
9. (b) Chambers, R. D.; Chivers, T. J. Chem. Soc. 1965, 3933.
10. Pivalaldehyde was a more suitable oxidant than other aliphatic aldehydes and ketones. Although benzaldehyde was also a good oxidant, it was not easy to remove excess benzaldehyde and benzyl alcohol produced after the oxidation
11. (a) Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1993, 577.
12. (b) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
13. (c) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
14. (d) Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1996, 721.
15. (e) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.
16. The following representative procedure was used: To a white suspension of 1 (3.6 mg, 0.01 mmol), magnesium sulfate (120 mg, 1.0 mmol), and 2 (159 μL, 1.0 mmol) in dry toluene (2 mL) was added pivalaldehyde (326 μL, 3.0 mmol) at ambient temperature under Ar. After being stirred for 3 h, the reaction mixture was diluted with aqueous sodium hydrogen carbonate (5 mL) and extracted twice with ether (5 mL each time). The combined organic phase was dried over magnesium sulfate, filtered, and evaporated. The product was purified by column chromatography on silica gel using pentane-ether (7:1) as the eluant (149 mg of 3, 99% yield).