G. Bianchini et al. / Tetrahedron Letters 45 (2004) 2351–2353
2353
(
Table 2, entries 2, 3 vs 5, 6). It is noteworthy to
3. Herrmann, W. A.; Fischer, R. W.; Scherer, W.; Rouch,
M. U. Angew. Chem., Int. Ed. Engl. 1993, 32, 1157–1160.
emphasize that, in the oxidation of 2, catalysts I and II
showed both high conversion values of substrate and
very good yields of product 6 (Table 2, entries 5, 6), even
if usually a catalytic species loses part of its activity after
the heterogenization process. These results are in
accordance with data previously obtained by us, in the
oxidation of cardanol derivatives with H
poly(4-vinylpyridine) supported MTO systems.
conclusion, to the best of our knowledge, this article
describes the first reported example in literature dealing
with the C–H insertion reactions of H O by means of
4
5
6
7
. Murray, R. W.; Iyanar, K.; Chen, J.; Wearing, J. T.
Tetrahedron Lett. 1995, 36, 6415–6418.
. Schuchardt, U.; Mandelli, D.; ShulÕpin, G. B. Tetrahedron
Lett. 1996, 37, 6487–6490.
. Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.;
Sadun, C. J. Org. Chem. 2002, 67, 1323–1332.
. (a) Saladino, R.; Neri, V.; Mincione, E.; Filippine, P.
Tetrahedron 2002, 58, 8493–8500; (b) Saladino, R.;
Mincione, E.; Attanasi, O. A.; Filippone, P. Pure Appl.
Chem. 2003, 75, 261–268; (c) Saladino, R.; Neri, V.;
Pelliccia, A. R.; Mincione, E. Tetrahedron 2003, 59, 7403–
2 2
O by use of
7b
In
2
2
7
408; (d) Bernini, R.; Mincione, E.; Cortese, M.; Saladino,
R.; Gualandi, G.; Belfiore, M. C. Tetrahedron Lett. 2003,
4, 4823–4825.
heterogeneous rhenium derivatives. Further work is
therefore in progress, in order to exploit further on this
efficient and environmentally friendly procedure.
4
8
9
. Compounds I and II were prepared as reported in Ref. 6.
In summary, MTO (256 mg, 1.0mmol) was added to a
suspension of the appropriate resin (1.0g) in ethanol
(
4 mL). The mixture was stirred for 1 h using a magnetic
Acknowledgement
stirrer. The solvent was removed by filtration, and the
catalyst was washed with ethyl acetate and finally dried
under high vacuum.
We are grateful to MIUR 40% for the financial support.
. The reaction mixtures have been analyzed by a Hewlett
Packard 6890Series gas chromatograph equipped with a
FID, using a 30m · 0.32 mm · 0.25 lm film thickness
(cross-linked 5% phenylmethylsiloxane) column and nitro-
gen as carrier gas. The identification of the peaks by GC–
MS has been performed by means of a Varian 2000 GC-
MAS instrument, using the same column. Yields and
conversions of the reactions have been quantified using
n-octane as internal standard, or when necessary, after
chromatographic purification.
References and notes
1
2
. For some recent examples of H
carbons, see: (a) ShulÕpin, G. B. Comptes Rendus Chimie
003, 6, 163–178; (b) Nizova, G. V.; Bolm, C.; Ceccarelli,
S.; Pavan, C.; ShulÕpin, G. B. Adv. Synth. Catal. 2002, 344,
99–905.
. For general reviews, see: (a) Rom ~a o, C. C.; K u€ hn, F. E.;
Herrmann, W. A. Chem. Rev. 1997, 97, 3197–3246; (b)
Owens, G. S.; Arias, J.; Abu-Omar, M. M. Catal. Today
2 2
O oxidation of hydro-
2
8
10. See for recent examples: (a) Revital, B. D.; Ronny, N.
Angew. Chem., Int. Ed. Engl. 2003, 42, 92–95; (b) Ishii, Y.;
Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.;
Nishiyama, Y. J. Org. Chem. 1995, 60, 3934–3935.
2
000, 55, 317–363.