The synthesis of arylketones via Friedel-Crafts acyldegermylation

Synlett

Volumn , Issue 14, 2005, Pages 2167-2170

  Spivey, Alan C ^a   Gripton, Christopher J G ^b   Noban, Catherine ^a   Parr, Nigel J ^c  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SHEFFIELD   (United Kingdom)

^c GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Arylgermanes; Electrophilic aromatic substitution; Friedel Crafts acylation; Oligothiophenes; Solid phase synthesis

Indexed keywords

2 METHYLACETOPHENONE; 2 PYRIDYLGERMANE; 2 THIOPHENYLDITOLYLGERMANE; 2 TRIMETHYLGERMYL 4 METHOXYACETOPHENONE; 2,4 DIMETHYLACETOPHENONE; 2,6 DIMETHYLACETOPHENONE; 3 GERMYLETHYL BENZOATE; 3 METHYLACETOPHENONE; 3,5 DIMETHYLACETOPHENONE; 4 ANISYLDIMETHYLGERMANE; 4 METHOXYACETOPHENONE; 4 METHYLACETOPHENONE; ACETOPHENONE DERIVATIVE; GERMANIUM DERIVATIVE; KETONE DERIVATIVE; SILANE DERIVATIVE; THIOPHENE DERIVATIVE; TIN DERIVATIVE; TRIMETHYLGERMANIUM BROMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON; FRIEDEL CRAFTS REACTION; SOLID PHASE SYNTHESIS; STEREOCHEMISTRY;

EID: 24744451188     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872258     Document Type: Article

References (39)

1. Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. Gil, C.; Bräse, S. Curr. Opin. Chem. Biol. 2004, 8, 230.
3. Spivey, A. C.; Diaper, C. M.; Rudge, A. J. Chem. Commun. 1999, 835.
4. Spivey, A. C.; Diaper, C. M.; Rudge, A. J. J. Org. Chem. 2000, 65, 5253.
5. Spivey, A. C.; Srikaran, R.; Diaper, C. M.; Turner, D. J. Org. Biomol. Chem. 2003, 1, 1638.
6. (a) Spivey, A. C.; Turner, D. J.; Turner, M. L.; Yeates, S. Org. Lett. 2002, 4, 1899.
7. (b) Spivey, A. C.; Turner, D. J.; Turner, M. L.; Yeates, S. Synlett 2004, 111.
8. Katz, H. E.; Bau, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359.
9. (a) Dallaire, C.; Brook, M. A. Organometallics 1990, 9, 2873.
10. (b) Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332.
11. Eaborn, C.; Pande, K. C. J. Chem. Soc. 1960, 1566.
12. (a) Austin, J. D.; Eabrn, C.; Smith, J. D. J. Chem. Soc. 1963, 4744.
13. 3 reported here have subsequently been shown to be in error: see ref. 11c, 11d, 17.
14. For reviews of acyldesilylation see: (a) Eaborn, C. J. Organomet. Chem. 1975, 100, 43.
15. (b) Chan, T. H.; Fleming, I. Synthesis 1979, 761.
16. (c) Häbich, D.; Effenberger, F. Synthesis 1979, 841.
17. (d) Bennetau, B.; Donogues, J. Synlett 1993, 171.
18. Neumann, W. P.; Hillgärtner, H.; Baines, K. M.; Dicke, R.; Vorspohl, K.; Kobs, U.; Nussbeutel, U. Tetrahedron 1989, 45, 951.
19. 3 see: (a) Maire, J.; Marrot, J.; Nabet, R. Bull. Soc. Chim. Fr. 1981, 429.
20. 3 see: Marsubara, S.; Yoshino, H.; Utimoto, K.; Oshima, K. Synlett 2000, 495.
21. Félix, G.; Laguerre, M.; Dunogues, J.; Calas, R. J. Chem. Res., Synop. 1980, 236.
22. Boymond, L.; Rottlander, M.; Cahiez, G.; Knochel, P. Angew. Chem. Int. Ed. 1998, 37, 1701.
23. Subjection of 2-TMG-4-methoxyacetophenone 12 to aluminium(III) chloride/AcCl to see if a second acyl group could be installed by ipso-degermylation resulted in the formation of no identifiable products.
24. Bennetau, B.; Krempp, M.; Dunogues, J. J. Organomet. Chem. 1987, 334, 263.
25. Bassindale, A. R.; Eaborn, C.; Walton, D. R. M.; Young, D. J. J. Organomet. Chem. 1969, 20, 49.
26. (a) Egorochkin, A. N.; Razuvaev, G. A. Russ. Chem. Rev. 1987, 56, 846.
27. (b) Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.
28. Data for Arylgermanes. (a) For compounds 2a, 2f, see: Moerlein, S. M. J. Organomet. Chem. 1987, 319, 29.
29. (b) For compounds 2b, 2c, see: Bennett, S. W.; Eaborn, C.; Jackson, R. A.; Pearce, R. J. Organomet. Chem. 1971, 28, 59.
30. 74Ge: 224.0620; found: 224.0623.
31. (d) For compound 2g, see: Moerlein, S. M. J. Org. Chem. 1987, 52, 664.
32. (e) For compound 2h, see: Riedmiller, F.; Jockisch, A.; Schmidbaur, H. Z. Naturforsch., B: Chem. Sci. 1999, 54, 13.
33. 2: 269.0597; found: 269.0588. For compounds 16,17, see ref. 6b.
34. Data for Acetyl Derivatives. (a) For compounds 3, 5, 7, 9, see: Cacchi, S.; Fabrizi, O.; Gavazza, F.; Goggiamani, A. Org. Lett. 2003, 5, 289.
35. (b) For compound 4, see: Buchwald, S. L.; Watson, B. T.; Lum, R. T.; Nugent, W. A. J. Am. Chem. Soc. 1987, 109, 7137.
36. For compound 6, see: Brook, M. A.; Henry, C. Tetrahedron 1996, 52, 861.
37. (d) For compound 8, see: Friedman, L.; Koca, R. M. J. Org. Chem. 1968, 33, 1255.
38. 2: 268.0519; found: 268.0521.
39. 18OSI: 337.0123; found: 337.0120.