Y. Sato et al. / Tetrahedron 68 (2012) 7077e7081
7081
3of was obtained in 87% yield when the reaction was carried out
using 10 equiv of 2f against 1o (Scheme 1).
OMe
OMe
OH
Ph Ph
Ph
1o
2 mmol
NaHSO4/SiO2
When 1,2,3,4-tetrahydro-1-naphthol (1p) was used as an alky-
lating agent for the reaction of 2h, 3ph was produced in 38% yield
along with unexpected product 5 (entry 15 and Scheme 2). When
2 mmol of 1p was stirred in DCE in the presence of NaHSO4/SiO2 at
30 ꢀC for 0.5 h, 5 was produced in 57% yield along with 6 (26%)
(Scheme 3, (Eq. 1)). Compound 5 was also formed by dimerization
of 6. When a mixture of 6 and NaHSO4/SiO2 was stirred at 30 ꢀC for
0.5 h in DCE, 5 was obtained in 85% yield. Reaction of 6 with 1p
using NaHSO4/SiO2 gave 5 in 81% yield (Scheme 3, (Eqs. 2 and 3)).
We interested in this direct coupling of alkene and alcohol. 1a also
reacted with 6 under the same conditions to give 7 in 72% yield
(Scheme 3, (Eq. 4)). These reactions are now under investigations.
+
DCE
80°C, 16h
Ph Ph
Ph
2f
20 mmol
3of
Y.= 87 %
Scheme 1.
OMe
OMe
Conclusion
+
+
1p
2h
In conclusion, we developed a simple and efficient procedure for
alkylation of aromatics with alcohols using NaHSO4/SiO2 and various
triaryl methanes were prepared. NaHSO4/SiO2 was easily recovered
from the reaction mixture and regenerated by simple treatment and
could be reused more than eight times without activity loss.
5
3ph
Scheme 2.
Supplementary data
1H NMR, 13C NMR, MS, IR, and elemental analysis are available.
Supplementary data associated with this article can be found in the
NaHSO4/SiO2
+
1p
(1)
5
57 %
DCE
30 °C, 0.5 h
6
26 %
References and notes
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NaHSO4/SiO2
(2)
(3)
DCE
30 °C, 0.5 h
6
5
85 %
NaHSO4/SiO2
+
1p
1a
5
DCE
80 °C, 1 h
81 %
6
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Ph
Ph
NaHSO4/SiO2
+
(4)
DCE
30 °C, 0.5 h
6
7
72 %
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Scheme 3.