4
Tetrahedron
spectra data associated with this article can be found, in the
12. Kang, S-K.; Lee, S-W.;Ryu, H-C. Chem. Commun. 1999,
online version
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13. Braga, A. L.; Vargas, F.; Zeni, G.; Silveira, C. C.;
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Acknowledgments
The authors thank the São Paulo Research Foundation
(FAPESP – 2012/00424-2, 2010/15677-8) for financial
support and the Conselho Nacional de Auxílio a Pesquisa
(CNPq) for a fellowship (HAS - 308320/2010-7).
References
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19. General procedure for the [3+2]-cycloaddition
reaction: To a two-necked 25-mL round-bottom flask under a
nitrogen atmosphere containing CuI (0.190 g, 1 mmol), THF
(4 mL), organic azide (1.1 mmol) and acetylene (1 mmol),
PMDETA (0.21 mL, 1 mmol) was added and the reaction
mixture stirred at room temperature. The reaction time was
determined by monitoring TLC. The reaction mixture was
then diluted with ethyl acetate and washed with aqueous
NH4Cl. The organic phase was collected, dried with MgSO4,
filtered and the solvent removed under vacuum. Purification
was undertaken by silica gel chromatography (eluting with
ethyl acetate/ hexane 1:9). 5-(butyltellanyl)-1,4-diphenyl-1H-
1,2,3-triazole (2a). The product was obtained as a white solid at a
yield of 71%. mp 104 °C. 1H NMR (CDCl3, 300 MHz) (ppm):
7.94 (d, J = 1.5 Hz, 1H); 7.91 (t, J = 1.5 Hz, 1H); 7.47-7.31 (m,
8H); 2.37 (t, J = 7.5 Hz, 2H) 1.27 (qn, J = 7.5 Hz, 2H); 0.98 (sx, J
= 7.5 Hz, 2H) 0.60 (t, J = 7.5 Hz, 3H). 13C NMR (CDCl3, 75 MHz)
(ppm): 154.0; 138.0; 131.4; 129.7; 129.1 (2C); 128.4 (5C); 126.4
(2C); 99.7; 32.9; 24.5; 13.0; 11.2. 125Te NMR (CDCl3, 94.69
MHz) (ppm): 268.4. HRMS calcd for C18H19N3Te + H+:
408.0719. Found: 408.0717. IR (cm-1): 3011, 2413, 1524,
1219, 767.
20. General procedure for the Te/Li exchange reaction: To
a two-necked 50-mL round-bottom flask under a nitrogen
atmosphere, n-BuLi (0.22 mL, 0.5 mmol, 2.2728 mol/L) was
added to a solution of 2a (0.20 g, 0.5 mmol) in THF (10 mL)
at -78 °C. After 60 min of stirring at -78 °C, anisaldehyde
(0.068 g, 0.5 mmol) was added and the mixture stirred for 12
h at room temperature, before being diluted with ethyl acetate
and washed with aqueous NH4Cl. The organic phase was
collected, dried with MgSO4, filtered and the solvent removed
under vacuum. Purification was performed by silica gel
chromatography, eluting with ethyl acetate / hexane.22,23 1,2,3-
triazol-5-yl)(4-methoxyphenyl)methanol (3b): The product
was obtained as a white solid at a yield of 91%. mp 114°C. 1H
NMR (CDCl3, 300 MHz) (ppm): 7.69-7.65 (m, 2H); 7.37-
7.25 (m, 8H); 6.90 (d, J = 8.6 Hz, 2H); 6.63 (d, J = 8.6 Hz,
2H); 6.16 (s, 1H); 3.68 (s, 3H). 13C NMR (CDCl3, 75 MHz)
(ppm): 158.9; 146.0; 136.6; 135.7; 132.2; 130.5; 129.5; 128.8
(2C); 128.5 (2C); 128.5 (2C); 128.2; 127.0 (2C); 128.2 (2C);
113.6 (2C); 65.6; 55.2; HRMS calcd for C22H19N3O2 + H+:
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