8084
R. Cano et al. / Tetrahedron 67 (2011) 8079e8085
4.4.1. Phenylmethanol (7a)29. Colourless oil; IR (cmꢂ1): 3324, 1495,
1453, 1207; 1H NMR (300 MHz, CDCl3):
2.62 (s, br, 1H), 4.59 (s,
CDCl3): d 16.5, 20.9,127.3 (2C),129.6 (2C),134.7,135; EI-MS m/z: 138
d
(Mþ, 100%), 123 (30), 92 (10), 91 (57), 79 (11), 77 (10).
2H), 7.25e7.3 (m, 5H); 13C NMR (75 MHz, CDCl3):
d 65, 126.9 (2C),
127.5, 128.4 (2C), 140.8; EI-MS m/z: 108 (Mþ, 62%), 107 (48), 79 (68),
Acknowledgements
77 (100).
This work was financially supported by the Spanish Ministerio
de Ciencia y Tecnología Spain (Projects CTQ2007-65218/BQU;
CTQ2011-24151 and Consolider Ingenio 2010 CSD2007-00006),
Generalitat Valenciana (G.V. PROMETEO/2009/039 and FEDER).
R.C. thanks to G.V. for a fellowship through the PROMETEO pro-
gram. We gratefully acknowledge the polishing of our English by
Mrs. Oriana C. Townley.
4.4.2. (4-Methoxyphenyl)methanol (7b)16j. Colourless oil; IR
(cmꢂ1): 3335, 1586, 1511, 1243, 1173; 1H NMR (300 MHz, CDCl3):
d
2.57 (s, br, 1H), 3.77 (s, 3H), 4.53 (s, 2H), 6.85 (d, J¼8.6 Hz, 2H), 7.23
(d, J¼8.6 Hz, 2H); 13C NMR (75 MHz, CDCl3):
d 55.1, 64.6, 113.8 (2C),
128.5 (2C),133.1,158.9; EI-MS m/z: 138 (Mþ, 88%),137 (61),136 (76),
135 (100), 77 (74).
4.4.3. (4-Chlorophenyl)methanol (7c)16h. Colourless solid; mp
68e71 ꢀC (hexane), IR (cmꢂ1): 3337, 1490, 1450, 798; 1H NMR
Supplementary data
(300 MHz, CDCl3):
d
2.1 (s, br, 1H), 4.63 (s, 2H), 7.27 (d, J¼8.6 Hz,
Supplementary data associated with this article can be found in
clude MOL files and InChiKeys of the most important compounds
described in this article.
2H), 7.32 (d, J¼8.6 Hz, 2H); 13C NMR (75 MHz, CDCl3):
d 64.4, 128.2
(2C), 128.6 (2C), 133.3, 139.2; EI-MS m/z: 144 (Mþþ1, 16%), 143 (Mþ,
13%), 142 (78), 141 (40), 140 (65), 139 (92), 125 (18), 113 (30), 112
(17), 111 (54), 107 (56), 105 (10), 89 (15), 79 (64), 77 (100).
References and notes
4.4.4. Cyclopentylmethanol (7d)30. Colourless solid; mp 121e123 ꢀC
(hexane), IR (cmꢂ1): 3341, 1196; 1H NMR (300 MHz, CDCl3):
ꢀ
1. For recent reviews, see: (a) Multicomponent Reactions; Zhu, J., Bienayme, H.,
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1.2e1.25, 1.5e1.6, 1.7e1.75 (3m, 2, 4 and 2H), 2e2.15 (m, 1H), 2.5
ꢀ
(s, br, 1H), 3.48 (d, J¼6.3 Hz, 2H); 13C NMR (75 MHz, CDCl3):
d 25.3
€
(2C), 29 (2C), 42, 67.1; EI-MS m/z: 100 (Mþ, 4%), 99 (54), 98 (33), 81
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4.4.5. Decan-1-ol (7e)31. Colourless oil; IR (cmꢂ1): 3326, 1465, 1377,
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Ramon, D. J.; Riente, P.; Yus, M. Mol. Diversity 2010, 14, 411e424; (i) Isambert, N.;
1056, 721; 1H NMR (300 MHz, CDCl3):
d
0.88 (t, J¼6.5 Hz, 3H),
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1.25e1.35 (m, 14H), 1.56 (p, J¼6.9 Hz, 2H), 2.1 (s, 1H), 3.61 (q,
J¼4.9 Hz, 2H); 13C NMR (75 MHz, CDCl3):
d 14, 22.6, 25.7, 29.3, 29.4,
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(48), 84 (52), 83 (83), 82 (31), 71 (17), 70 (96), 69 (85), 68 (32), 67
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d
4.13 (d, J¼6.2 Hz, 2H), 5.38
(t, J¼6.1 Hz, 1H), 7.15e7.3, 7.45e7.5, 7.55e7.6, 7.85e7.9 (4m, 5, 2, 1
and 2H, respectively); 13C NMR (75 MHz, CDCl3):
47, 126.9 (2C),
d
127.6, 127.7 (2C), 128.5 (2C), 129 (2C), 132.5, 136.2, 139.7; EI-MS
m/z: 247 (Mþ, 0.2%), 106 (100), 104 (12), 91 (14), 79 (15), 78
(13), 77 (37), 51 (11).
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4.5. General procedure for the sulfoxide reduction process
To a stirred solution of aryl methyl sulfoxide (8, 1 mmol) in
toluene (2 mL) were added PdOeFe3O4 (50 mg, 1.2 mol % of Pd) and
PMHS (4 mmol, 0.24 mL). The resulting mixture was stirred at
130 ꢀC during a week. The catalyst was removed by a magnet and
the resulting mixture was quenched with water and extracted with
EtOAc. The organic phases were dried over MgSO4, followed by
evaporation under reduced pressure to remove the solvent. The
corresponding products 9 were purified by chromatography on
silica gel (hexane/ethyl acetate).
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4.5.1. Methyl(phenyl)sulfane (9a)19b. Colourless oil; IR (cmꢂ1):
2011, 353, 57e63; (h) Firouzabadi, H.; Iranpoor, N.; Gholinejad, M.; Hoseini, J.
1581, 1529, 736; 1H NMR (300 MHz, CDCl3):
d
2.48 (s, 3H), 7.1e7.15,
7.25e7.3 (2m, 1 and 4H, respectively); 13C NMR (75 MHz, CDCl3):
15.8, 125, 126.6 (2C), 128.8 (2C), 138.7; EI-MS m/z: 124 (Mþ, 100%),
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Adv. Synth. Catal. 2011, 353, 125e132; (i) Cano, R.; Ramon;, D. J.; Yus, M. Synlett,
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ꢁ
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4.5.2. Methyl(p-tolyl)sulfane (9b)32. Pale yellow oil; IR (cmꢂ1):
11. (a) Uheida, A.; Iglesias, M.; Fontas, C.; Hidalgo, M.; Salvado, V.; Zhang, Y.;
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1583, 1528, 763; 1H NMR (300 MHz, CDCl3):
d 2.3 (s, 3H), 2.45 (s,
3H), 7.09 (d, J¼8.1 Hz, 2H), 7.18 (d, J¼8.1 Hz, 2H); 13C NMR (75 MHz,