1806
F.-E. Chen et al.
SHORT PAPER
(9) (a) Meshram, H. M. Synthesis 1992, 943. (b) Bandgar, B.
P.; Jagtap, S. R.; Ghodeshwar, S. B.; Wadganonkar, P. P.
Synth. Commun. 1995, 25, 2993. (c) Fukuzawa, S. I.;
Yamaishi, Y.; Furuya, H.; Terao, K.; Iwasaki, F.
Tetrahedron Lett. 1997, 38, 7203. (d) Erman, M. B.; Snow,
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(e) Jose, B.; Sulatha, M. S.; Pillai, P. M.; Prathapan, S. Synth.
Commun. 2000, 30, 1509. (f) Desai, D. G.; Swami, S. S.;
Makala, G. D. Synth. Commun. 2000, 30, 1623.
Table 2 Optimization of Reaction Conditions for the Synthesis of
Benzonitrile (2c) from Benzyl Alcohol (1c)a
Entry Solvent
Catalyst
Temp Time Yieldb
(°C) (h)
(%)
50
90
60
43
45
70
42
45
56
37
46
69
44
48
75
41
0c
1
2
i-PrOH
i-PrOH
i-PrOH
i-PrOH
MeCN
MeCN
MeCN
CH2Cl2
CH2Cl2
CH2Cl2
THF
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel copper formate
nickel formate
10
25
40
60
10
25
40
10
25
40
10
25
40
10
25
40
25
8
1.5
1.5
1.5
8
(g) Sampath Kumar, H. M.; Subba Reddy, B. V.; Tirupathi
Reddy, P.; Yadav, J. S. Synthesis 1999, 586. (h) Chaudhari,
S. S.; Akamanchi, K. G. Synth. Commun. 1999, 29, 1741.
(i) Wang, E. C.; Lin, G. J. Tetrahedron Lett. 1998, 39, 4047.
(j) Talukdar, S.; Hsu, J. L.; Chou, T.; Fang, J. M.
Tetrahedron Lett. 2001, 42, 1103. (k) Forey, H. G.; Datlon,
D. R. J. Chem. Soc., Chem. Commun. 1973, 628.
(l) Kukhar, V. P.; Pasternak, V. I. Synthesis 1974, 563.
(m) Shinozaki, H.; Imaizumi, M.; Tajima, M. Chem. Lett.
1983, 929. (n) Katritzky, A. R.; Zhang, G. F.; Fan, W. Q.
Org. Prep. Proc. Int. 1993, 25, 315. (o) Lai, G.; Bhamare,
N. K.; Anderson, W. K. Synlett 2001, 230.
3
4
5
6
1.5
1.5
7
8
10
9
2
(10) (a) Ganboa, I.; Palomo, G. Synth. Commun. 1983, 13, 999.
(b) Olah, G. A.; Keumi, T. Synthesis 1979, 112.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
1.5
8
(c) Sosnovsky, G.; Krogh, J. A.; Umhoefer, S. G. Synthesis
1979, 722. (d) Garboa, I.; Palomo, C. Synth. Commun. 1983,
13, 219. (e) Saednya, A. Synthesis 1982, 190. (f) Miller, C.
P.; Kaufman, D. H. Synlett 2000, 1169. (g) Das, B.;
Madhusudhan, R. P. Synlett 2000, 1599. (h) Feng, J. C.;
Liu, B.; Dai, L.; Bian, N. S. Synth. Commun. 1998, 28,
3765. (i) Desai, D. G.; Swami, S. S.; Mahale, G. D. Synth.
Commun. 2000, 30, 1623. (j) Veverkova, E.; Toma, S.
Synth. Commun. 2000, 30, 3109. (k) Chakraborti, A. K.;
Kaur, G. Tetrahedron 1999, 25, 13265. (l) Tose, B.;
Sulatha, M. S.; Pillai, M.; Prathapan, S. Synth. Commun.
2000, 30, 1509. (m) Bose, D. S.; Narsaiah, A. V.
Tetrahedron Lett. 1998, 39, 6533.
THF
2
THF
1.5
8
DMF
DMF
2
DMF
1.5
toluene
toluene
i-PrOH
i-PrOH
i-PrOH
i-PrOH
i-PrOH
i-PrOH
10
reflux 25
0c
(11) (a) Lehnert, W. Tetrahedron Lett. 1971, 1501.
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4685.
(14) (a) Feldhues, U.; Schafer, H. J. Synthesis 1982, 145.
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Tetrahedron Lett. 1990, 31, 3305. (d) Gao, S.; Herzig, D.;
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64, 1713.
25
25
25
25
25
25
1.5
75
73
78
55
53
0c
nickel oxalate
2
nickel citrate
2
nickel sulfate
2
nickel chloride
2
none
1.5
a All reactions were preformed according to the typical procedure.
b Yield refer to isolated pure product.
c Compound 1c was recovered unchanged from the reaction mixture.
M. E.; Torley, I. W.; Wrenn, S. J. Med. Chem. 1990, 33,
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Synthesis 2002, No. 13, 1804–1806 ISSN 0039-7881 © Thieme Stuttgart · New York