PAPER
Arenediazonium o-Benzenedisulfonimides in Heck-Type Arylation of Allylic Alcohols
3451
2-(4-Methoxyphenyl)-1-phenylpropan-1-one (4n)38
Trace.
References
(1) For example, see: (a) Tsuji, J. Palladium Reagents and
Catalysts: New Perspectives for the 21st Century; Wiley:
Chichester, 2004, Chapter 3, 108–176; and references cited
therein. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev.
2000, 100, 3009; and references cited therein. (c) Alonso,
F.; Beletskaya, I. P.; Yus, M. Tetrahedron 2005, 61, 11771.
(2) Melpolder, J. B.; Heck, R. F. J. Org. Chem. 1976, 41, 265.
(3) (a) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976, 41,
273. (b) Chalk, A. J.; Magennis, S. A. J. Org. Chem. 1976,
41, 1206.
(4) (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
(b) Jeffery, T. Tetrahedron Lett. 1991, 32, 2121.
(5) Zhao, H.; Cai, M. Z.; Hu, R. H.; Song, C. S. Synth. Commun.
2001, 31, 3665.
(6) (a) Calò, V.; Nacci, A.; Lopez, L.; Napola, A. Tetrahedron
Lett. 2001, 42, 4701. (b) Calò, V.; Nacci, A.; Monopoli, A.;
Spinelli, M. Eur. J. Org. Chem. 2003, 1382.
(7) Bouquillon, S.; Ganchegui, B.; Estrine, B.; Hénin, F.;
Muzart, J. J. Organomet. Chem. 2001, 634, 153.
(8) (a) Berthiol, F.; Doucet, H.; Santelli, M. Tetrahedron Lett.
2004, 45, 5633. (b) Berthiol, F.; Doucet, H.; Santelli, M.
Tetrahedron 2006, 62, 4372.
MS (EI): m/z (%) = 240 (5) [M+], 135 (100) [M – COC6H5]+.
3-(4-Methoxyphenyl)-1-phenylpropan-1-one (3n)36,38,39
Oil; yield: 0.07 g (19%).
IR: 1690 (C=O) cm–1.
1H NMR: d = 3.03 (t, J = 7.3 Hz, 2 H), 3.29 (t, J = 7.6 Hz, 2 H), 3.80
(s, 3 H), 6.86 (d, J = 8.2 Hz, 2 H), 7.18 (d, J = 8.4 Hz, 2 H), 7.42–
7.58 (m, 3 H), 7.97 (d, J = 6.7 Hz, 2 H).
MS (EI): m/z (%) = 240 (50) [M+], 121 (100) [M – CH2COC6H5]+.
Arylation of 2c with 1j
3-Ethoxy-1-(2-methoxyphenyl)-3-phenylprop-1-ene (8f) and
3-Ethoxy-3-(2-methoxyphenyl)-1-phenylprop-1-ene (8g)
Inseparable mixture; oil; yield: 0.10 g (23%).
1H NMR: d = 1.22 (t, J = 7.0 Hz, 6 H), 3.42–3.58 (m, 4 H), 3.78 (s,
3 H), 3.79 (s, 3 H), 4.90 (d, J = 7.6 Hz, 1 H), 5.35 (d, J = 6.6 Hz, 1
H), 6.26 (dd, J = 16.0, 6.6 Hz, 1 H), 6.27 (dd, J = 16.0, 7.6 Hz, 1 H),
6.58 (d, J = 15.8 Hz, 1 H), 6.79–6.99 (m, 5 H), 7.12–7.47 (2 m, 14
H).
13C NMR: d = 157.0, 142.1, 137.3, 133.1, 131.2, 130.4, 130.0,
129.0, 128.6, 127.6, 127.3, 127.1, 127.0, 126.3, 125.7, 121.1, 120.8,
111.1, 110.8, 83.3, 75.8, 64.3, 64.1, 55.7, 15.6.
MS (EI): m/z (%) = 268 (30) [M+], 135 (100).
MS (EI): m/z (%) = 268 (20) [M+], 105 (100).
(9) Kikukawa, K.; Matsuda, T. Chem. Lett. 1977, 159.
(10) Kikukawa, K.; Nagira, K.; Wada, F.; Matsuda, T.
Tetrahedron 1981, 37, 31.
(11) Hu, R. H.; Liu, X. L.; Cai, M. Z. Jiangxi Shifan Daxue
Xuebao, Ziran Kexueban 2001, 25, 246; Chem. Abstr. 2001,
136, 355024.
(12) Masllorens, J.; Bouquillon, S.; Roglans, A.; Hénin, F.;
Muzart, J. J. Organomet. Chem. 2005, 690, 3822.
(13) Bräse, S.; Schroen, M. Angew. Chem. Int. Ed. 1999, 38,
1071.
2-(2-Methoxyphenyl)-1-phenylpropan-1-one (4o)
Trace.
MS (EI): m/z (%) = 240 (10) [M+], 135 (100) [M – COC6H5]+.
(14) (a) Barbero, M.; Degani, I.; Fochi, R.; Perracino, P.
(CNRItaly) WO 9839312, 1998; Chem. Abstr., 1998, 129,
244942. (b) Barbero, M.; Crisma, M.; Degani, I.; Fochi, R.;
Perracino, P. Synthesis 1998, 1171. (c) Barbero, M.;
Degani, I.; Dughera, S.; Fochi, R. Synthesis 2004, 2386; and
references cited therein.
(15) (a) Artuso, E.; Barbero, M.; Degani, I.; Dughera, S.; Fochi,
R. Tetrahedron 2006, 62, 3146. (b) Dughera, S. Synthesis
2006, 1117.
3-(2-Methoxyphenyl)-1-phenylpropan-1-one (3o)38
Oil; yield: 0.07 g (20%).
IR: 1691 (C=O) cm–1.
1H NMR: d = 3.03 (t, J = 7.2 Hz, 2 H), 3.29 (t, J = 7.1 Hz, 2 H), 3.85
(s, 3 H), 6.86–6.94 (m, 2 H), 7.19–7.24 (m, 2 H), 7.43–7.57 (m, 3
H), 8.00 (d, J = 6.7 Hz, 2 H).
MS (EI): m/z (%) = 240 (60) [M+], 121 (100) [M – CH2COC6H5]+.
(16) (a) Dearden, J. C.; Nicholson, R. M. J. Pharm. Pharmacol.
1984, 36, 713. (b) Ducki, S.; Hadfield, J. A.; Hepworth, L.
A.; Lawrence, N. J.; Liu, C.-Y.; McGown, A. T. Bioorg.
Med. Chem. Lett. 1997, 7, 3091. (c) Murthy, Y. V. S. N.;
Meah, Y.; Massey, V. J. Am. Chem. Soc. 1999, 121, 5344.
(17) For a palladium-catalyzed synthesis of dihydrochalcones
see: Briot, A.; Baehr, C.; Brouillard, R.; Wagner, A.;
Mioskowski, C. J. Org. Chem. 2004, 69, 1374; and
references cited therein for their medicinal properties.
(18) Tsuji, J. Palladium Reagents and Catalysts: New
Perspectives for the 21st Century; Wiley: Chichester, 2004,
Chapter 4, 431–469; and references therein.
(19) (a) Barbero, M.; Degani, I.; Diulgheroff, N.; Dughera, S.;
Fochi, R. Synthesis 2001, 585. (b) Barbero, M.; Degani, I.;
Diulgheroff, N.; Dughera, S.; Fochi, R.; Migliaccio, M. J.
Org. Chem. 2000, 65, 5600.
(20) Gallardo, I.; Guirado, G.; Marquet, J. Eur. J. Org. Chem.
2002, 261.
Arylation of 2b with 1i
Reaction carried out in MeOH. Isolated from the mixture was 9a.
3-Methoxy-1-(4-methoxyphenyl)oct-1-ene (9a)
1H NMR: d = 0.72–0.85 (m, 3 H), 1.10–1.55 (m, 8 H), 3.24 (s, 3 H),
3.75 (s, 3 H), 5.83 (dd, J = 8.0, J = 15.8 Hz, 1 H), 6.40 (d, J = 16 Hz,
1 H), 6.80 (d, J = 8.8 Hz, 2 H), 7.28 (d, J = 8.8 Hz, 2 H).
MS (EI): m/z (%) = 248 (20) [M+], 177 (100) [M – C5H11]+.
Arylation of 2d and 2e with 1a and 1i
Structure and purity of the isolated products 10a–d, 11a,b, 12a–c,
and 13b (isolated as an inseparable mixture with 12b), reported in
Table 6, were confirmed by comparison of their spectral data (MS
and 1H NMR) with those reported in literature from arenediazonium
tetrafluoroborates.11,12
(21) Romesberg, F. E.; Flanagan, M. E.; Uno, T.; Schultz, P. G.
J. Am. Chem. Soc. 1998, 120, 5160.
(22) Barker, S. D.; Norris, R. K. Aust. J. Chem. 1983, 36, 527.
(23) Boatman, S.; Harris, T. M.; Hauser, C. R. J. Org. Chem.
1965, 30, 3321.
Acknowledgment
This work was supported by Italian MIUR and by Università degli
Studi di Torino.
(24) Bunce, R. A.; Herron, D. M.; Ackerman, M. L. J. Org.
Chem. 2000, 65, 2847.
Synthesis 2006, No. 20, 3443–3452 © Thieme Stuttgart · New York