Tayebee et al.
FULL PAPER
molecule from it in the second step. Finally, one ester
molecule was eliminated from the metallacycle, and the
primarily zinc ion was recovered.
(d) Chakraborti, A. K.; Gulhane, R.; Shivani Synlett 2003,
1805.
Orita, A.; Sakamoto, K.; Hamada, Y.; Mitsutome, A.; Otera,
J. Tetrahedron 1999, 55, 2910.
9
In summary, we have demonstrated the catalytic ef-
ficacy of commercial ZnO towards O-acylation of al-
cohols with benzoyl chloride under very mild reaction
conditions. Some important features of the present
methodology were simple reaction procedure, good
yields of products in short reaction times, using inex-
pensive and nonpoisonous metal oxide, and moisture
compatibility of the protocol. Thus, this methodology
represents an eco-friendly alternative to many existing
10 Forsyth, S. A.; MacFarlane, D. R.; Thomson, R. J.; von
Itzstein, M. Chem. Commun. 2002, 714.
11 Yamada, S.; Sugaki, T.; Matsuzaki, K. J. Org. Chem. 1996,
61, 5932.
12 Allevi, P.; Ciuffreda, P.; Longo, A.; Anastasia, M.
Tetrahedron: Asymmetry 1998, 9, 2914.
13 (a) Chakraborti, A. K.; Gulhane, R. Tetrahedron Lett. 2003,
44, 3521.
(b) Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003,
22, 1896.
(c) Kumar, P.; Pandey, R. K.; Bodas, M. S.; Dongare, M. K.
Synlett 2001, 206.
procedures and is suitable for industrial purposes. Our
+
new important findings proved that Zn2 was the cata-
lytically active species in homogeneous benzoylation of
alcohols. However, the catalytic efficiency of commer-
cial zinc oxide in homogeneous benzoylation of alco-
hols was indeed superior to some of the previously re-
ported protocols using other mineral oxides.23-29
14 (a) Alizadeh, M. H.; Kermani, T.; Tayebee, R. Monatsh.
Chem. 2007, 138, 165.
(b) Alizadeh, M. H.; Tayebee, R. Monatsh. Chem. 2006, 137,
1063.
(c) Tayebee, R.; Alizadeh, M. H. Monatsh. Chem. 2007, 138,
763.
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Chin. J. Chem. 2010, 28, 1247— 1252