Synthesis of symmetrical ketones from Grignard reagents and 1,1′-carbonyldiimidazole

Synthesis

Volumn , Issue 14, 2009, Pages 2316-2318

  Bottalico, Daniela ^a   Fiandanese, Vito ^a   Marchese, Giuseppe ^a   Punzi, Angela ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

1,1 carbonyldiimidazole; Acylations; Coupling; Grignard reactions; Ketones

Indexed keywords

ACYLATIONS; CARBONYLDIIMIDAZOLE; COUPLING REACTION; GRIGNARD REACTIONS; GRIGNARD REAGENT; STRAIGHT-FORWARD METHOD;

ACYLATION; OPTICAL FILTERS;

KETONES;

9 HEPTADECANONE; BIS(2 THIENYL)METHANONE; BIS(4 FLUOROPHENYL)METHANONE; CARBONYLDIIMIDAZOLE; DICYCLOHEXYLMETHANONE; HENICOSAN 11 ONE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; PENTACOSAN 13 ONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 67651112167     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1216815     Document Type: Article

References (30)

1. (a) O'Neill, B. T. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M.; Fleming, I.; Schreiber, S. L., Eds.; Pergamon: Oxford, 1991, 397.
2. (b) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999.
3. (c) Dieter, R. K. Tetrahedron 1999, 55, 4177; and references cited therein.
4. (d) Smith, B. M.; March, J. Advanced Organic Chemistry, 5th ed.; Wiley: Chichester, 2001.
5. (a) Shirley, D. A. Org. React. 1954, 8, 28.
6. (b) Jorgenson, M. J. Org. React. 1970, 18, 1.
7. For some recent examples on the reactions of organometallic reagents with the most commonly used acyl chlorides or Weinreb amides, see: (a) Dieter, R. K.; Sharma, R. R.; Yu, H.; Gore, V. K. Tetrahedron 2003, 59, 1083.
8. (b) Zhang, Y.; Rovis, T. J. Am. Chem. Soc. 2004, 126, 15964.
9. (c) Taillier, C.; Bellosta, V.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2145.
10. (d) Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. J. Organomet. Chem. 2004, 689, 326.
11. (e) Oh, C. H.; Reddy, R. Tetrahedron Lett. 2004, 45, 8545.
12. (f) Wang, X.-j.; Zhang, L.; Sun, X.; Xu, Y.; Krishnamurty, D.; Senanayake, C. H. Org. Lett. 2005, 7, 5593.
13. (g) Conrad, K.; Hsiao, Y.; Miller, R. Tetrahedron Lett. 2005, 46, 8587.
14. (h) Kangani, C. O.; Kelley, D. E.; Day, B. W. Tetrahedron Lett. 2006, 47, 6289.
15. (i) Crestey, F.; Stiebing, S.; Legay, R.; Collot, V.; Rault, S. Tetrahedron 2007, 63, 419.
16. For some recent examples involving other carboxylic acid derivatives and organometallic reagents, see: (a) Katritzky, A. R.; Le, K. N. B.; Mohapatra, P. P. Synthesis 2007, 3141.
17. (b) Katritzky, A. R.; Le, K. N. B.; Khelashvili, L.; Mohapatra, P. P. J. Org. Chem. 2006, 71, 9861.
18. (c) Werner, T.; Barrett, G. M. J. Org. Chem. 2006, 71, 4302.
19. (d) Wang, D.; Zhang, Z. Org. Lett. 2003, 5, 4645.
20. (e) Wittenberg, R.; Srogl, J.; Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 3033.
21. (f) MaGee, D. I.; Mallais, T. C.; Eic, M. Tetrahedron: Asymmetry 2003, 14, 3177.
22. Bottalico, D.; Fiandanese, V.; Marchese, G.; Punzi, A. Synlett 2007, 974; and references cited therein.
23. (a) Staab, H. A.; Bauer, H.; Schneider, K. M. Azolides in Organic Synthesis and Biochemistry; Wiley-VCH: Weinheim, 1998.
24. (b) Bonini, B. F.; Comes-Franchini, M.; Fochi, M.; Mazzanti, G.; Ricci, A.; Varchi, G. Synlett 1998, 1013; and references cited therein.
25. Ishiyama, T.; Hartwig, J. J. Am. Chem. Soc. 2000, 122, 12043.
26. Kangani, C. O.; Day, B. W. Org. Lett. 2008, 10, 2645.
27. Tartaglia, S.; Pace, F.; Scafato, P.; Rosini, C. Org. Lett. 2008, 10, 3421.
28. Aldrich Catalogue, 2009-2010.
29. TCI Europe Catalogue, 2008-2009.
30. Rao, M. L. N.; Periasamy, M. Tetrahedron Lett. 1995, 36, 9069.