SiCl4-Zn induced reductive coupling of carbonyl compounds: novel and efficient routes for one-pot syntheses of 1,2,3-triaryl-2-propen-1-ones and pinacolones at room temperature

Tetrahedron Letters

Volumn 48, Issue 25, 2007, Pages 4395-4398

  Salama, Tarek A ^a   Elmorsy, Saad S ^a   Khalil, Abdel Galel M ^a  

^a Mansoura University   (Egypt)

Author keywords

1,2,3 Triaryl 2 propen 1 ones; Carbonyl compounds; Pinacolones; Rearrangement; Reductive coupling; Tetrachlorosilane; Zinc

Indexed keywords

1,2,3 TRIARYL 2 PROPEN 1 ONE DERIVATIVE; ALDEHYDE; ALKANONE; CARBONYL DERIVATIVE; KETONE; PINACOLONE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SILICON TETRACHLORIDE; UNCLASSIFIED DRUG; ZINC;

ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; ROOM TEMPERATURE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 34248640260     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.092     Document Type: Article

References (44)

1. Ladipo F.T. Curr. Org. Chem. 10 (2006) 965-980
2. Gansauer A., and Bluhm H. Chem. Rev. 100 (2000) 2771-2788
3. Furstner A., and Bogdanovic B. Angew. Chem., Int. Ed. 35 (1996) 2442-2469
4. Wirth T. Angew. Chem., Int. Ed. 35 (1996) 61-63
5. McMurry J.E. Chem. Rev. 89 (1989) 1513-1524
6. Harter P., Latzel K., Spiegler M., and Herdtweck E. Polyhedron 17 (1998) 1141-1148
7. Leimner J., and Weyerstahl P. Chem. Ber. 115 (1982) 3697-3705
8. Szymoniak J., Besancon J., and Moise C. Tetrahedron 48 (1992) 3867-3876
9. Sato R., Nagaoka T., and Saito M. Tetrahedron Lett. 31 (1990) 4165-4168
10. Dutta D.K., and Kanwar D. Tetrahedron Lett. 41 (2000) 6227-6229
11. Grant A.A., Allukian M., and Fry A.J. Tetrahedron Lett. 43 (2002) 4391-4393
12. Salama T.A., Elmorsy S.S., Khalil A.M., Girges M.M., and El-Ahl A.S. Synth. Commun. 37 (2007) 1313-1319
13. Salama T.A., El-Ahl A.S., Khalil A.M., Girges M.M., Lackner B., Steindl C., and Elmorsy S.S. Monatsh. Chem. 134 (2003) 1241-1252
14. Salama, T. A.; Elmorsy, S. S.; El-Ahl, A. S.; Khalil, A. M. 2nd International Conference on Multi-Component Coupling Reactions, Combinatorial and Related Chemistry (MCR); Genova, Italy, 2003, p 86.
15. Elmorsy S.S., Khalil A.M., Girges M.M., and Salama T.A. Tetrahedron Lett. 38 (1997) 1071-1074
16. Denmark S.E., and Fan Y. J. Org. Chem. 70 (2005) 9667-9676
17. Denmark S.E., Beutner G.L., Wynn T., and Eastgate M.D. J. Am. Chem. Soc. 127 (2005) 3774-3789
18. Lee S.H., Jang B.-B., and Kafafi Z.H. J. Am. Chem. Soc. 127 (2005) 9071-9078
19. Acocella M.R., De Rosa M., Massa A., Palombi L., Villano R., and Scettri A. Tetrahedron 61 (2005) 4091-4097
20. Tokuoka E., Katani S., Matsunogo H., Ishizuka T., Hashimoto S., and Nakajima M. Tetrahedron: Asymmetry 16 (2005) 2391-2392
21. Kim B.J., and Mattseon D.S. Angew. Chem., Int. Ed. 43 (2004) 3056-3058
22. Denmark S.E., and Heemstra Jr. J.R. Org. Lett. 5 (2003) 2303-2306
23. Matteson D.S., and Kim G.Y. Org. Lett. 4 (2002) 2153-2155
24. Nakajma M., Saito M., Uemura M., and Hashimoto S. Tetrahedron Lett. 43 (2002) 8827-8829
25. Gupta H.K., Reginato N., Ogini F.O., Brydges S., and McGlinchey M.J. Can. J. Chem. 80 (2002) 1546-1554
26. Denmark S.E., Wynn T., and Jellerichs B.G. Angew. Chem., Int. Ed. 40 (2001) 2255-2256
27. Magarian R.A., Overacre L.B., Singh S., and Meyer K.L. Curr. Med. Chem. 1 (1994) 61-104
28. Mittal S., Durani S., and Kapil R.S. J. Med. Chem. 28 (1985) 492-497 and references cited therein
29. Tomita M., Minami S., and Uyeo S. J. Chem. Soc. (C) (1969) 183-188
30. Rieke R.D., and Kim S.H. J. Org. Chem. 63 (1998) 5235-5239
31. Afonso C.A.M., Motherwell W.B., O'Shea D.M., and Roberts L.R. Tetrahedron Lett. 33 (1992) 3899-3902
32. Smith C.L., Arnett J., and Ezike J. J. Chem. Soc., Chem. Commun. (1980) 653-654
33. Srinivas K., Krishna K.L., Sivaprasad A., and Rao P.S. Indian J. Chem. 37B (1998) 936
34. Afonso C.A.M., Motherwell W.B., and Roberts L.R. Tetrahedron Lett. 33 (1992) 3367-3370
35. Banerjee A.K., Sulbaran de Carrasco M.C., Frydrych-Hauge C.S.V., and Motherwell W.B. J. Chem. Soc., Chem. Commun. (1986) 1803-1805
36. 3O (387.65): C, 65.06; H, 3.38%. Found: C, 65.14; H, 3.32%.
37. Black W.B., and Lutz R.E. J. Am. Chem. Soc. 75 (1953) 5990-5997
38. Yates P., Levi E.M., and Shapiro B.L. Can. J. Chem. 52 (1974) 3343
39. Fulton J.D., Robinson R., Oldham J.W.H., and Obbelohde A.R. J. Chem. Soc. (1939) 200-202
40. Newkome G.R., and Robinson J.M. J. Org. Chem. 41 (1976) 2536-2542
41. Angle S.R., and Neitzel M.L. J. Org. Chem. 65 (2000) 6458-6461
42. Bencze W., and Allen M. J. Org. Chem. 22 (1957) 1352
43. So J.-H., Park M.-K., and Boudjouk P. J. Org. Chem. 53 (1988) 5871-5875
44. Ogata Y., Kawasaki A., Haba M., and Tsujino T. J. Org. Chem. 42 (1977) 2423-2425