Arenediazonium o-Benzenedisulfonimides and Triorganoindium
FULL PAPER
[5] a) S. Darses, J. Tuyet, J.-P. Genet, Tetrahedron Lett. 1996, 37,
3857–3860; b) S. Darses, J. Tuyet, J.-L. Brayer, J.-P. Demoute,
J.-P. Genet, Bull. Soc. Chim. Fr. 1996, 133, 1095–1102; c) S.
Sengupta, S. Bhattacharyya, J. Org. Chem. 1997, 62, 3405–
3406; d) S. Sengupta, S. K. Sadhukhan, Tetrahedron Lett. 1998,
39, 715–719; e) K. Kikukawa, K. Kono, F. Wada, T. Matsuda,
J. Org. Chem. 1983, 48, 1333–1336; f) N. A. Bumagin, L. I.
Sukhomlinova, T. P. Tolstaya, I. P. Beletskaya, Russ. J. Org.
Chem. 1994, 30, 1605–1609.
[6] a) N. Miyaura, T. Yanagi, A. Suzuki, Synth. Commun. 1981,
11, 513–519; b) N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95,
2457–2484; c) A. R. Martin, Y. Yang, Acta Chem. Scand. 1993,
47, 221–230.
[7] a) D. Millstein, J. K. Stille, J. Am. Chem. Soc. 1978, 100, 3636–
3638; b) D. Millstein, J. K. Stille, J. Am. Chem. Soc. 1979, 101,
4981–4991; c) J. K. Stille, Angew. Chem. Int. Ed. Engl. 1986, 25,
508–524; d) T. N. Mitchell, Synthesis 1992, 803–815; e) F. W.
Forman, I. Sucholeiki, J. Org. Chem. 1995, 60, 523–528; f) V.
Farina, V. Krishnamurthy, W. J. Scott, Org. React. 1997, 50, 1–
652.
[8] a) P. Cintas, Synlett 1995, 1087–1096 and references cited
therein; b) J. A. Marshall, Chemtracts: Org. Chem. 1997, 10,
481–496; c) C.-J. Li, T.-H. Chan Organic Reactions in Aqueous
Media, Wiley, New York, 1997, chapter 4, 64–114.
umn, eluting with petroleum ether/diethyl ether (9:1). Details are
shown in Table 3.
Collateral Proofs: (a) To a solution of tributylphenyltin (9a,
5.5 mmol, 2.02 g) or phenylboronic acid (9b, 5.5 mmol, 0.61 g) in
THF (20 mL) was added, under vigorous stirring in one portion
and at room temperature, 4-methoxybenzenediazonium o-benzene-
disulfonimide (1d, 5 mmol, 1.77 g). The obtained suspension was
stirred at room temperature for 24 h; a test of azo coupling with 2-
naphthol was positive. The suspension was heated at reflux for 8 h,
but a test of azo coupling was still positive. The unreacted 4-me-
thoxybenzenediazonium o-benzenedisulfonimide (1d) was reco-
vered by filtration through a Buchner funnel (Table 5, Entries 1
and 3). (b) 4-methoxybiphenyl (3da) was obtained, as reported in
the literature[1a,5a] (Table 5, Entries 2 and 4). (c) (E)-1-(4-meth-
oxyphenyl)-2-phenyldiazene (4da) was obtained, as reported in the
literature[19] (Table 5, Entry 7). (d) To phenylmagnesium bromide
(9c, 1 solution in THF, 5.5 mmol, 5.5 mL) was added THF
(20 mL). Bis(triphenylphosphane)palladium(II) dichloride (0.17 g,
0.25 mmol) and 4-methoxybenzenediazonium o-benzenedisulfon-
imide (1d, 5 mmol, 1.77 g) were added at room temperature with
vigorous stirring in one portion. The salt dissolved at once, and the
resulting solution became very dark. Stirring was maintained for
50 min at room temperature until a test of azo coupling with 2-
naphtol was negative. GC, GC-MS and TLC (petroleum ether/di-
ethyl ether, 9:1) analyses of the reaction mixture showed (E)-1-(4-
methoxyphenyl)-2-phenyldiazene {4da, MS (EI): m/z = 212 [M]+}
as the major product, besides 4-methoxybenzene {MS (EI): m/z =
108 [M]+} as the minor product. The usual workup afforded pure
(E)-1-(4-methoxyphenyl)-2-phenyldiazene (4da, 0.80 g, 75% yield).
The same results were obtained with palladium(II) acetate as the
catalyst (Table 5, Entry 8). (e) To phenyllithium (9d, 1.9 solution
in butyl ether, 5.5 mmol, 2.9 mL) was added THF (20 mL). Bis(tri-
phenylphosphane)palladium(II) dichloride (0.17 g, 0.25 mmol) and
4-methoxybenzenediazonium o-benzenedisulfonimide (1d, 5 mmol,
1.77 g) were added at 0 °C with vigorous stirring in one portion.
The salt dissolved at once, and the resulting solution became very
dark. Stirring was maintained for 5 min at room temperature until
a test of azo coupling with 2-naphtol was negative. GC, GC-MS
and TLC (petroleum ether/diethyl ether, 9:1) analyses of the reac-
tion mixture showed the presence of 4-methoxybenzene as the only
product. After the usual workup only tars were recovered. The
same results were obtained with palladium(II) acetate as the cata-
lyst (Table 5, Entry 9) and without catalyst (Table 5, Entry 10).
[9]
M. A. Pena, J. Perez Sestelo, L. A. Sarandeses, Synthesis 2003,
780–784.
[10] L. A.Paquette, in: Green Chemistry; Frontiers in Benign Chemi-
cal Synthesis and Processing (Eds.: P. T. Anastas, T. C. William-
son), Oxford University Press, Oxford, 1998, chapter 15, 250–
264.
[11] a) I. Perez, J. Perez Sestelo, M. A. Maestro, A. Mourinho, L. A.
Sarandeses, J. Org. Chem. 1998, 63, 10074–10076; b) S. Araki,
K. Shimizu, S.-J. Jin, Y. Butsugan, J. Chem. Soc. Chem. Com-
mun. 1991, 824–825.
[12] a) S. Araki, A. Imai, K. Shimizu, M. Yamada, A. Mori, Y.
Butsugan, J. Org. Chem. 1995, 60, 1841–1847; b) N. Fujiwara,
Y. Yamamoto, J. Org. Chem. 1999, 64, 4095–4101; c) E. Klaps,
W. Schmid, J. Org. Chem. 1999, 64, 7537–7546; d) K. Takami,
H. Yorimitsu, K. Oshima, Org. Lett. 2002, 4, 2993–2995.
[13] D. Rodriguez, J. Perez Sestelo, L. A. Sarandeses, J. Org. Chem.
2003, 68, 2518–2520.
[14]
[15]
[16]
[17]
I. Perez, J. Perez Sestelo, L. A. Sarandeses, J. Am. Chem. Soc.
2001, 123, 4155–4160.
I. Perez, J. Perez Sestelo, L. A. Sarandeses, Org. Lett. 1999, 1,
1267–1269.
D. Rodriguez, J. Perez Sestelo, L. A. Sarandeses, J. Org. Chem.
2004, 69, 8136–8139.
a) M. A. Pena, I. Perez, J. Perez Sestelo, L. A. Sarandeses,
Chem. Commun. 2002, 2246–2247; b) M. A. Pena, J. Perez Ses-
telo, L. A. Sarandeses, Synthesis 2005, 485–492.
P. H. Lee, S. W. Lee, K. Lee, Org. Lett. 2003, 5, 1103–1106.
M. Barbero, I. Degani, S. Dughera, R. Fochi, P. Perracino,
Synthesis 1998, 1235–1237.
[18]
[19]
Acknowledgments
This work was supported by Italian MIUR and by University of
Torino.
[20]
[21]
[22]
[23]
[24]
A. Nunez, A. Sanchez, C. Burgos, J. Alvarez-Builla, Tetrahe-
dron 2004, 60, 6217–6224.
G. De Luca, G. Renzi, R. Cipollini, A. Pizzabiocca, J. Chem.
Soc. Perkin Trans. 1 1980, 1901–1903.
E. Anklam, K. D. Asmus, L. W. Robertson, J. Fluorine Chem.
1988, 38, 209–216.
C. Bjorklund, M. Nilsson, Acta Chem. Scand. 1968, 22, 2338–
2346.
Y. Tamura, M. W. Chun, K. Inoue, J. Minamikawa, Synthesis
1978, 822.
[1] a) S. Dughera, Synthesis 2006, 1117–1124; b) E. Artuso, M.
Barbero, I. Degani, S. Dughera, R. Fochi, Tetrahedron 2006,
62, 3146–3157.
[2] Reviews: a) J. Hassan, M. Sevignon, C. Gozzi, E. Schulz, M.
Lemaire, Chem. Rev. 2002, 102, 1359–1469; b) S. Stanforth,
Tetrahedron 1998, 54, 263–303 and references cited therein.
[3] Reviews: a) Metal-Catalyzed Cross-Coupling Reactions (Eds.:
F. Diederich, P. J. Stang), Wiley-VCH, Weinheim, 1998; b) H.
Geissler, in: Transition Metal for Organic Synthesis (Eds.: M.
Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, chapter 2.10,
158–183; c) J. Tsuji, Palladium Reagents and Catalysts, Wiley,
Chichester, U. K., 2004, chapter 3, 288–348 and references
cited therein.
[25]
[26]
M. J. S. Dewar, A. N. James, J. Chem. Soc. 1958, 917–921.
G. W. K. Cavill, D. H. Solomon, J. Chem. Soc. 1958, 1404–
1406.
[27]
[28]
F. R. Shaw, E. E. Turner, J. Chem. Soc. 1932, 285–297.
A. Burawoy, I. Markowitsch-Burawoy, J. Chem. Soc. 1936, 36–
39.
[29]
[4] K. Ritter, Synthesis 1993, 735–762.
J. J. Ritter, F. O. Ritter, J. Am. Chem. Soc. 1931, 53, 670–671.
Eur. J. Org. Chem. 2006, 4884–4890
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