G. Hua, J. D. Woollins / Tetrahedron Letters 48 (2007) 3677–3679
3679
Se
Se
R1
R1
R2
Se
Ph
Ph
Se
Ph
Se
Ph
Se
Se
O
Se
O
S
P
Ph
P
P
P
P
S
R2
Se
Se
WR
R1
R1
Se
S
Se S
R1
R2
R2
Ph
R2
Ph
O
Ph
P
O
S
O
O
O
Ph
Se
R1
O
O
P
P
P
P
S
O
P
O
R2
O
Se
O
O
Ph
Ph
R1
R2
R1
Sen
Se
S
S
+
R2
Scheme 1.
Tetrahedron 2005, 61, 3587–3591; (c) Kikuchi, S.; Hashi-
moto, Y. Synlett 2004, 1267–1269; (d) Hashimoto, Y.;
Konishi, H.; Kikuchi, S. Synlett 2004, 1264–1266; (e)
Hashimoto, Y.; Kikuchi, S. Chem. Lett. 2002, 126–127.
thus in refluxing toluene elemental selenium would be
expelled to give stable sulfides (1b–12b).
In conclusion, the deoxygenation of a series of sulfox-
ides to sulfides was effectively promoted by WR under
mild conditions in a good to excellent yield. The reaction
was found to be a very useful approach in organic syn-
thesis because of the easy work-up, mild conditions,
high selectivity and high conversion of substrates.
6. (a) Harrison, D. J.; Tam, N. C.; Vogels, C. M.; Langler, R.
F.; Baker, R. T.; Decken, A.; Westcott, S. A. Tetrahedron
Lett. 2004, 45, 8493–8496; (b) Palazzi, C.; Colombo, L.;
Gennari, C. Tetrahedron Lett. 1986, 27, 1735–1738; (c)
Suzuki, I.; Yamamoto, Y. J. Org. Chem. 1993, 58, 4783–
4784; (d) Shi, M.; Jiang, J. K.; Cui, S. C.; Feng, Y. S. J.
Chem. Soc., Perkin Trans. 1 2001, 390–393.
7. Iranpoor, N.; Firouzabadi, H.; Reza Shaterian, H. J.
Chem. Soc., Chem. Commun. 2002, 67, 2826–2830.
8. (a) Fitzmaurice, J. C.; Williams, D. J.; Wood, P. T.;
Woollins, J. D. J. Chem. Soc., Chem. Commun. 1988, 741–
743; (b) Gray, I. P.; Bhattacharyya, P.; Slawin, A. M. Z.;
Woollins, J. D. Chem. Eur. J. 2005, 11, 6221–6227.
9. (a) Baxter, I.; Hill, A. F.; Malget, J. M.; White, A. J. P.;
Williams, D. J. J. Chem. Soc., Chem. Commun. 1997,
2049–2050; (b) Hill, A. F.; Malget, J. M. J. Chem. Soc.,
Chem. Commun. 1996, 1177–1178; (c) Bhattacharyya, P.;
Woollins, J. D. Tetrahedron Lett. 2001, 42, 5949–5951; (d)
Bhattacharyya, P.; Slawin, A. M. Z.; Woollins, J. D.
Inorg. Chem. Commun. 2004, 7, 1171; (e) Bethke, J.;
Karaghiosoff, K.; Wessjohann, L. A. Tetrahedron Lett.
2003, 44, 6911–6913.
Acknowledgement
We are grateful to the Engineering and Physical Science
Research Council (EPSRC, U.K.) for financial support.
Supplementary data
Supplementary data associated with this article can be
References and notes
10. Hua, G.; Li, Y.; Slawin, A. M. Z.; Woollins, J. D. Org.
Lett. 2006, 8, 5251–5254.
1. (a) Boyd, D. R.; Sharma, N. D.; Haughey, S. A.;
Kennedy, M. A.; Malone, J. F.; Shepherd, S. D.; Allen,
C. C. R.; Dalton, H. Tetrahedron 2004, 60, 549–559; (b)
Karimi, B.; Zareyee, D. Synthesis 2003, 335–336; (c)
Nicolaou, K. C.; Kuombis, A. E.; Synder, S. A.; Simon-
sen, K. B. Angew. Chem., Int. Ed. 2000, 39, 2529–2533; (d)
Abo, M.; Dejima, M.; Asano, F.; Okubo, A.; Yamazaki,
S. Tetrahedron: Asymmetry 2000, 11, 823–828; (e) Kuk-
ushkin, V. Y. Coord. Chem. Rev. 1995, 139, 375–407.
2. Black, S.; Harte, E. M.; Hudson, B.; Wartofsky, L. J. Biol.
Chem. 1960, 235, 2910–2916.
3. (a) Drabowicz, J.; Togo, H.; Mikolajczyk, M.; Oae, S.
Org. Prep. Proced. Int. 1984, 16, 171–175; (b) Madesclaire,
M. Tetrahedron 1988, 44, 3783–6537.
4. (a) Firouzabadi, H.; Karimi, B. Synthesis 1999, 500–502;
(b) Yoo, B.; Choi, K. H.; Kim, D. Y.; Choi, K. I.; Kim, J.
H. Synth. Commun. 2003, 33, 53–57; (c) Shimizu, M.;
Shibuya, K.; Hayakawa, R. Synlett 2000, 1437–1438; (d)
Miller, S. J.; Collier, T. R.; Wu, W. Tetrahedron Lett.
2000, 41, 3781–3783.
11. (a) Darout, K. E. Org. Lett. 2005, 7, 203–206; (b)
Foreman, M. St. J.; Slawin, A. M. Z.; Woollins, J. D. J.
Chem. Soc., Dalton Trans. 1999, 1175–1184; (c) Foreman,
M. St. J.; Slawin, A. M. Z.; Woollins, J. D. J. Chem. Soc.,
Chem. Commun. 1997, 855–856; (d) Bhattacharyya, P.;
Slawin, A. M. Z.; Woollins, J. D. Chem. Eur. J. 2002, 8,
2705–2711; (e) Bhattacharyya, P.; Slawin, A. M. Z.;
Woollins, J. D. Angew. Chem., Int. Ed. 2000, 39, 1973–
1975; (f) Bhattacharyya, P.; Slawin, A. M. Z.; Woollins, J.
D. J. Organomet. Chem. 2001, 623, 116–119; (g) Bhatta-
charyya, P.; Slawin, A. M. Z.; Woollins, J. D. J. Chem.
Soc., Dalton Trans. 2001, 300–303; (h) Bhattacharyya, P.;
Novosad, J.; Phillips, J. R.; Slawin, A. M. Z.; Williams, D.
J.; Woollins, D. J. J. Chem. Soc., Dalton Trans. 1995,
1607–1613.
12. (a) Hua, G.; Li, Y.; Slawin, A. M. Z.; Woollins, J. D. Eur.
J. Inorg. Chem. 2007, 891–897; (b) Hua, G.; Li, Y.; Slawin,
A. M. Z.; Woollins, J. D. Chem. Commun. 2007, 1465–
1467.
13. Hua, G.; Li, Y.; Slawin, A. M. Z.; Woollins, J. D. Dalton
Trans. 2007, 1477–1480.
5. (a) Szmant, H. H.; Cox, O. J. Org. Chem. 1966, 31, 1595–
1598; (b) Kikuchi, S.; Konishi, H.; Hashimoto, Y.