J. Chil. Chem. Soc., 56, Nº 2 (2011)
REFERENCES AND NOTES
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Am. Chem. Soc. 95, 1296, (1973).
Scheme 3: One-pot synthesis of a-diketones from aldehydes.
Table 3: The synthesis of benzils in one-pot reaction.
8. D. G. Lee, V. S. Chang, Synthesis, 462, (1978).
9. (a) P. L. Anelli, S. Banfi, F. Montanari, S. Quici, J. Org. Chem. 54, 2970,
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1523, (1995).
Entry
Ar
Product
3a
Time(h)
Yield%
85
Mp(°C)
95-96
1
2
Ph
2
2
4-Me-C6H4
4-MeO-C6H4
4-OH-C6H4
4-Cl-C6H4
3-Br-C6H4
4-Br-C6H4
4-NO2-C6H4
3-Cl-C6H4
3-NO2-C6H4
Furan-2-yl
3b
80
103-105
130-131
---
3
3c
2.5
4
75
12. (a) W. Rigby, J. Chem. Soc. 793, (1951). (b) H. T. Clarke, E. E. Dreger,
Org. Synth. Coll. 1, 87, (1941).
4
3d
none
94
13. S. Baskaran, J. Das, S. Chandrasekaran, J. Org. Chem. 54, 5182, (1989).
14. X. B. Jing, X. Pan, Z. Li, Y. C. Shi, Syn. Commn. 39, 492, (2009).
15. (a) S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 109, 3612,
(2009). (b) F. E. Hahn, M. C. Jahnke, Angew. Chem. Int. Ed. 47, 3122,
(2008). (c) Topics in Organometallic Chemistry, Vol. 21; Glorius, F. Ed.;
Springer: Berlin, 2007; (d) R. E. Douthwaite, Coord. Chem. Rev. 251, 702,
(2007). (e) E. A. B. Kantchev, C. J. O’Brien, M. G. Organ, Angew. Chem.
Int. Ed. 46, 2768, (2007). (f) W. A. Herrmann, Angew. Chem. Int. Ed. 41,
1290, (2002).
5
3e
1.5
1.5
1.5
4
195-198
122-124
224-226
---
6
3f
86
7
3g
80
8
3h
trace
90
9
3i
1.5
4
114-116
---
10
11
3j
trace
85
16. (a) D. Enders, O. Niemeier, A. Henseler, Chem. Rev., 107, 5606, (2007).
(b) H. Clavier, S. P. Nolan, Annu. Rep. Prog. Chem., Scet. B. 103, 193,
(2007).
3k
1.5
165-166
17. K. Iwamoto; M. Hamaya. Tetrahedron Lett. 47, 7175, (2006).
CONCLUSIONS
In conclusion, as described above, we developed a one-pot synthesis of
benzils by the domino reaction of aldehydes with benzimidazolium salt as
catalyst and the oxygen in the air as oxidizing reagent. The present reaction
with its mild and metal-free conditions opens a novel green entry to synthesis
of benzils by simple procedure.
ACKNOWLEDGMENTS
This research was supported by the Cultivation and Construction Found
for the State Key Subject of Physical Chemistry.
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