Complex induced proximity effect enhancement in α-silyl carbanion generation. A general conversion of 2-silyl benzamides into 2-fluorosilylacetophenones

Tetrahedron Letters

Volumn 37, Issue 17, 1996, Pages 2915-2918

  Brough, Paul A ^a   Fisher, Stephen ^a   Zhao, Baoping ^a   Thomas, Ryan C ^a   Snieckus, Victor ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOPHENONE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; ORGANOSILICON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029878150     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00446-7     Document Type: Article

References (23)

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3. (a) Sieburth, S. McN.; Fensterbank, L. J. Org. Chem. 1993, 58, 6314 and references therein
4. (b) Wang, W. and Snieckus, V. J. Org. Chem. 1992, 57, 424.
5. ref 54b in Schlosser, M.; Choi, J.H.; Takagishi, S. Tetrahedron 1990, 46, 5648.
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8. (a) Gray, M.; Tinkl, M.; Snieckus, V. in Comprehensive Organomettalic Chemistry II, Vol. 11, Ed. McKillop, A., Pergamon, Oxford, 1995, pp 6-41.
9. (a) Fu, J.-m.; Zhao, B.-p.; Sharp, M.J.; Snieckus, V. J. Org. Chem. 1991, 56, 1683-1685.
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12. Wiberg, E.; Krüerke, U. Z. Naturoforsch B 1953, 8, 608. Mechanism: Scheim, U.; Porzel, A.; Ruhlmann, K. J. Organometal. Chem. 1988, 354, 31.
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15. In both cases, the silanols corresponding to 2 were isolated and characterized.
16. For anionic cyclization of diarylsulfones to thioxanthen-9-ones where, admittedly, ortho-acidity is higher, see Beaulieu, F.; Snieckus, V. J. Org. Chem. 1994, 59, 6508.
17. 3, 63% yield): Zhao, B.-p. Ph.D. Thesis, University of Waterloo, 1994.
18. Unrau, C.M.; Campbell, M.G.; Snieckus, V. Tetrahedron Lett. 1992, 33, 2773.
19. The ketone or enol corresponding to 9 is unknown.
20. Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4249. See also Suginome, M.; Matsunaga, S.-i.; Ito, Y. Synlett 1995, 941.
21. Tamao, K.; Ishida, N. Tetrahedron Lett. 1984, 25, 4249. See also Suginome, M.; Matsunaga, S.-i.; Ito, Y. Synlett 1995, 941.
22. 4) and concentrated in vacuo. The resulting yellow oil was dissolved in anhyd THF (10 mL) under nitrogen, boron trifluoride etherate (1.0 mL, 8.1 mmol) was added dropwise, and the reaction mixture was allowed to stand for 18 h. Workup and purification as above (except for the inclusion of a satd aq NaCl wash prior to drying) gave the product (760 mg, 85%) as a colorless solid, which was recrystallized from acetone-water.
23. We are grateful to NSERC Canada for support by way of Research Grant and NSERC/Monsanto Industrial Research Chair programs.