Fluorotetraphenylbismuth: A new reagent for efficient regioselective α-phenylation of carbonyl compounds

Journal of the American Chemical Society

Volumn 125, Issue 35, 2003, Pages 10494-10495

  Ooi, Takashi ^a   Goto, Ryoji ^a   Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BISMUTH DERIVATIVE; CARBONYL DERIVATIVE; FLUOROTETRAPHENYLBISMUTH; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0042357040     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja030150k     Document Type: Article

References (31)

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11. 1H NMR.
12. This is in sharp contrast to tetrakis(2-methoxyphenyl)bismuthonium halides (Cl, Br, and I) which are highly stabilized through the intramolecular coordination of the methoxy oxygen toward the bismuth center adopting a tetrahedral geometry. A large separation between the bismuth and halogen atoms was observed in these ionic compounds. See: Suzuki, H.; Ikegami, T.; Azuma, N. J. Chem. Soc., Perkin Trans. 1 1997, 1609.
13. 1 = 0.032.
14. 3 at room temperature revealed that each phenyl group was equivalent in solution. See the Supporting Information.
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18. For the advantages of the recently developed novel palladium-catalyzed arylation methods, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740. See also: (d) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953 and references therein.
19. For the advantages of the recently developed novel palladium-catalyzed arylation methods, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740. See also: (d) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953 and references therein.
20. For the advantages of the recently developed novel palladium-catalyzed arylation methods, see: (a) Palucki, M.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 11108. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1997, 119, 12382. (c) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740. See also: (d) Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2002, 41, 953 and references therein.
21. Only a few examples of this type of arylation have appeared: (a) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673.
22. Only a few examples of this type of arylation have appeared: (a) Chen, K.; Koser, G. F. J. Org. Chem. 1991, 56, 5764. (b) Iwama, T.; Birman, V. B.; Kozmin, S. A.; Rawal, V. H. Org. Lett. 1999, 1, 673.
23. Attempted reaction of 2-methylcyclohexanone with NaH (1.1 equiv) and tetraphenylbismuthonium tetrafluoroborate (1.1 equiv) in THF (0.3 M) at room temperature for 72 h resulted in the formation of 2-methyl-6-phenylcyclohexanone (5%, cis/trans mixture), 2-methyl-2-phenylcyclohexanone (18%), and 2-methyl-6,6-diphenylcyclohexanone (11%).
24. 8 at room temperature showed the appearance of the signal of trimethylsilyl fluoride at δ -154.21 ppm.
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26. For a recent impressive report on the synthesis of enolizable ethenylated products, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074. (b) Arisawa, M.; Miyagawa, C.; Yamaguchi, M. Synthesis 2002, 138. See also: (c) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. (d) Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. (e) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
27. For a recent impressive report on the synthesis of enolizable ethenylated products, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074. (b) Arisawa, M.; Miyagawa, C.; Yamaguchi, M. Synthesis 2002, 138. See also: (c) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. (d) Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. (e) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
28. For a recent impressive report on the synthesis of enolizable ethenylated products, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074. (b) Arisawa, M.; Miyagawa, C.; Yamaguchi, M. Synthesis 2002, 138. See also: (c) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. (d) Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. (e) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
29. For a recent impressive report on the synthesis of enolizable ethenylated products, see: (a) Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074. (b) Arisawa, M.; Miyagawa, C.; Yamaguchi, M. Synthesis 2002, 138. See also: (c) Millard, A. A.; Rathke, M. W. J. Am. Chem. Soc. 1977, 99, 4833. (d) Kosugi, M.; Hagiwara, I.; Migita, T. Chem. Lett. 1983, 839. (e) Hayashi, A.; Yamaguchi, M.; Hirama, M. Synlett 1995, 51.
30. For α-alkenylation of 1,3-dicarbonyl compounds, see: (a) Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. (b) Ochiai, M.; Shu, T.; Nagaoka, T.; Kitagawa, Y. J. Org. Chem. 1997, 62, 2130.
31. For α-alkenylation of 1,3-dicarbonyl compounds, see: (a) Moloney, M. G.; Pinhey, J. T. J. Chem. Soc., Chem. Commun. 1984, 965. (b) Ochiai, M.; Shu, T.; Nagaoka, T.; Kitagawa, Y. J. Org. Chem. 1997, 62, 2130.