Direct α-arylation of ketones: The reaction of cyclic ketone enolates with diphenyliodonium triflate

Tetrahedron Letters

Volumn 38, Issue 28, 1997, Pages 5061-5064

  Ryan, John H ^a   Stang, Peter J ^b  

^a JAMES COOK UNIVERSITY   (Australia)

^b UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPHENYLIODONIUM SALT; KETONE;

ACYLATION; ARTICLE; CYCLIZATION; KETOGENESIS; STOICHIOMETRY;

EID: 0030860221     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01105-2     Document Type: Article

References (27)

1. (a) Negishi, E.-I.; Akiyoshi, K. Chem. Lett., 1987, 1007.
2. (b) Nair, V; Turner, G. A.; Chamberlain, S. D. J. Am. Chem. Soc., 1987, 109, 7223.
3. (c) Kosugi, M.; Hagawara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn., 1984, 57, 242 and J. Chem. Soc., Chem. Commun., 1983, 344.
4. (c) Kosugi, M.; Hagawara, I.; Sumiya, T.; Migita, T. Bull. Chem. Soc. Jpn., 1984, 57, 242 and J. Chem. Soc., Chem. Commun., 1983, 344.
5. (d) Kiwajima, I.; Urabe, H. J. Am. Chem. Soc., 1982, 104, 6831.
6. (a) Rathke, M.; Vogiazoglou, D. J. Org. Chem., 1987, 52, 3697.
7. (b) Sacks, C. E.; Fuchs, P. L. J. Am. Chem. Soc., 1975, 97, 7372.
8. (a) Scamehorn, R. G.; Hardacre, J. M.; Lukanich, J. M.; Sharpe, L. R. J. Org. Chem., 1984, 49, 4881.
9. (b) Review: Bunnett, J. F. Acc. Chem. Res., 1978, 11, 413.
10. (c) Rossi, R. A.; Bunnett, J. F. J. Am. Chem. Soc., 1974, 96, 112.
11. (a) Semmelhack, M. F.; Bargar, T. J. Am. Chem. Soc., 1980, 102, 7765.
12. (b) Semmelhack, M. F.; Bargar, T. J. Org. Chem., 1977, 42, 1481.
13. (a) Huang, Y.-Z.; Zhou, Z.-L. in Comprehensive Organometallic Chemistry II, McKillop, A. Ed.; Pergamon: Oxford, 1995; Vol. 11, 503.
14. (b) Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron, 1988, 44, 3039.
15. (c) Barton, D. H. R.; Finet, J.-P.; Gianotti, C.; Halley, F. J. Chem. Soc., Perkin Trans. 1, 1987, 241.
16. (a) Morgan, J.; Pinhey, J. T.; Rowe, B. A. J. Chem. Soc., Perkin Trans, 1, 1997, 1005.
17. (b) Kozyrod, R. P.; Pinhey, J. T. Aust. J. Chem., 1985, 38, 1156.
18. (a) Chen, K; Koser, G. F. J. Org. Chem., 1991, 56, 5764
19. (b) Beringer, F. M.; Daniel, W. J.; Galton; S. A.; Rubin, G. J. Org. Chem., 1966, 31, 4315.
20. Recent Reviews: (c) Stang, P. J.; Zhdankin, V. V. Chem. Rev., 1996, 96, 1123.
21. (d) Koser, G. F. in The Chemistry of Halides, Pseudo-Halides and Azides, Suppl. D2; Patai, S.; Rappoport, Z. Eds.; Wiley-Interscience: Chichester, 1995; Chapter 21.
22. (e) Varvoglis, A. The Organic Chemistry of Polycoordinated Iodine; VCH: New York, 1992.
23. (a) Zhdankin, V. V.; Scheuller, M. C.; Stang, P. J. Tetrahedron Lett., 1993, 34, 6853.
24. (b) Stang, P. J.; Zhdankin, V. V.; Tykwinski, R.; Zefirov, N. S. Tetrahedron Lett., 1992, 33, 1419.
25. The arylation of ketone enolates with diphenyliodonium salts has been reported, but only in a dissertation: Manis, P. A. The Synthesis and Reactions of Sterically Hindered Silyl Enol Ethers. The Reaction of α-Azido Esters with Base. The Phenylation of Ketone Enolates with Diphenyliodonium Salts, Michigan State University, 1982.
26. 5 and styrene, were unsuccessful; the ratios of iodobenzene, 2c and 3c in the crude reaction product remained unchanged.
27. In accord with this proposal, the reaction of cyclohexanone with bis(2,4,6-trimethylphenyl)iodonium triflate under analogous conditions, gave only reduction, the reaction product consisting of a ca. 1:1:1 mixture of 1-iodo-2,4,6-trimethylbenzene, 1,3,5-trimethylbenzene and cyclohexanone.