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References and notes
6. General procedure for the synthesis of diaryl tellurides: A sealed tube containing a
1
.
(a) Petragnani, N.; Stefani, H. A. Tellurium in Organic Synthesis, 2nd ed.;
Academic Press: London, 2007; (b) Oba, M.; Tanaka, K.; Nishiyama, K.; Ando, W.
J. Org. Chem. 2011, 76, 4173–4177; (c) Stefani, H. A.; Pena, J. M.; Manarin, F.;
Ando, R. A.; Leal, D. M.; Petragnani, N. Tetrahedron Lett. 2011, 52, 4398–4401;
magnetic stirring bar was charged with aryl iodide (1.0 mmol), Te0 (1.0 mmol),
KOH (2.0 mmol), and DMSO (2 mL) under nitrogen. The reaction mixture was
heated in an oil bath at 110 °C and stirred at this temperature for 10 h. The
progress of the reaction was monitored by TLC via syringe. After the reaction
was complete, the reaction mixture was allowed to cool, and treated with
(
d) Oba, M.; Okada, Y.; Endo, M.; Tanaka, K.; Nishiyama, K.; Shimada, S.; Ando,
W. Inorg. Chem. 2010, 49, 10680–10686; (e) Kobayashi, K.; Deguchi, N.; Horn,
E.; Furukawa, N. Angew. Chem., Int. Ed. 1998, 37, 984–986; (f) Leonard, K. A.;
Zhou, F.; Detty, M. R. Organometallics 1996, 15, 4285–4292.
CH
2
Cl
2
2
and H O. The organic layer was washed with sat. NH
4
Cl and brine
solution, dried with Na
2
SO , and concentrated under vacuum. The residue was
4
purified by column chromatography on silica gel with an eluent consisting of
hexanes and ethyl acetate to afford the corresponding diaryl telluride product
in good to excellent yields. Bis(p-tolyl)telluride (1a). Light yellow solid, mp 72–
2
.
(a) Petragnani, N.; Stefani, H. A. Tetrahedron 2005, 61, 1613–1679; (b) Cunha, R.
L.; Gouvea, I. E.; Juliano, L. Ann. Braz. Acad. Sci. 2009, 81, 393–407.
You, Y.; Ahsan, K.; Detty, M. R. J. Am. Chem. Soc. 2003, 125, 4918–4927.
Frisell, H.; Engman, L. J. Mol. Struct. 2000, 526, 103–114.
3
4
5
.
.
.
1
7
(
1
3 °C; yield: 92%; H NMR (300 MHz, CDCl
3
), (ppm): 7.59 (d, J = 6 Hz, 4H), 7.03
), (ppm): 138.2, 137.8,
H14Te] 312.0158; found 312.0154.
13
d, J = 6 Hz, 4H), 2.33 (s, 6H). C NMR (75 MHz, CDCl
3
Kanda, T.; Engman, L.; Cotgreave, I. A.; Powis, G. J. Org. Chem. 1999, 64, 8161–
+
30.5, 110.8, 21.9. HRMS (EI): calcd for [C14
Dipyridinyl-3-telluride (1j). Pale yellow oil; yield: 84%; H NMR (300 MHz,
CDCl ), (ppm): 8.88 (s, 2H), 8.54 (d, J = 6 Hz, 2H), 8.00 (d, J = 6 Hz, 2H), 7.17 (m,
8
169.
1
6
7
8
.
.
.
Wieslander, E.; Engman, L.; Svensjo, E.; Erlansson, M.; Johansson, U.; Linden,
M.; Andersson, C.-M.; Brattsand, R. Biochem. Pharmacol. 1998, 55, 573–584.
Engman, L.; Kanda, T.; Gallegos, A.; Williams, R.; Powis, G. Anti-Cancer Drug Des.
3
13
2
(
H). C NMR (75 MHz, CDCl
3
), (ppm): 157.5, 149.3, 145.6, 125.0, 111.5. HRMS
285.9750; found 285.9753.
7. Bunnett, J. F.; Wamser, C. C. J. Am. Chem. Soc. 1967, 89, 6712–6718.
+
8 2
EI): calcd for [C10H TeN ]
2
001, 15, 323–330.
1
Andersson, C. M.; Hallberg, A.; Brattsand, R.; Cotgreave, I. A.; Engman, L.;
Persson, J. Bioorg. Med. Chem. Lett. 1993, 3, 2553–2558.