PAPER
Synthesis of Selenoesters from Diselenides
1081
1
H NMR (400 MHz, CDCl ): d = 7.62–7.53 (m, 5 H), 7.41–7.38 (m,
(3) Heppke, G.; Martens, J.; Praefcke, K.; Simon, H. Angew.
Chem., Int. Ed. Engl. 1977, 16, 318; Angew. Chem. 1977, 89,
328.
3
6
1
H), 6.76 (d, J = 16.0 Hz, 1 H).
3
C NMR (100 MHz, CDCl ): d = 190.7, 141.1, 135.8, 133.8, 130.9,
3
(
4) Pheninger, J.; Heuberger, C. Helv. Chim. Acta 1980, 63,
328.
1
29.3, 129.0, 128.9, 128.5, 126.2.
2
(
5) (a) Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.;
Fleming, I., Eds.; Pergamon: New York, 1991. (b) Krief, A.
In Comprehensive Organometallic Chemistry II, Vol. 11;
Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon:
New York, 1995, Chap. 13. (c) Miyaura, N. In Metal-
Catalyzed Cross-Coupling Reactions, Vol. 1; Meijere, A.;
Diederich, F., Eds.; Wiley-VCH: Weinheim, 2004, 41–123.
Se-Phenyl Ethaneselenoate
Yellow oil.15
1
H NMR (400 MHz, CDCl ): d = 7.53–7.49 (m, 2 H), 7.39–7.35 (m,
3
3
H), 2.49 (s, 3 H).
1
3
C NMR (100 MHz, CDCl ) d = 197.2, 136.1, 129.7, 129.3, 129.0,
3
3
4.4.
(
d) Bates, G. S.; Diakur, J.; Masamune, S. Tetrahedron Lett.
1
976, 49, 4423. (e) Mullen, G. P.; Luthra, N. P.; Dunlap, R.
Se-4-Tolyl Benzeneselenoate
Light yellow crystals; mp 72–73 °C (Lit. 71–72 °C).
1
6
B.; Odom, J. D. J. Org. Chem. 1985, 50, 811. (f) Silveira,
C. C.; Braga, A. L.; Larghi, E. L. Organometallics 1999, 18,
1
H NMR (400 MHz, CDCl ): d = 7.86 (d, J = 8.0 Hz, 2 H), 7.57–
3
5183. (g) Braga, A. L.; Martins, T. L. C.; Silveira, C. C.;
7
.52 (m, 1 H), 7.43–7.39 (m, 4 H), 7.18–7.16 (m, 2 H), 2.33 (s, 3 H).
Rodrigues, O. E. D. Tetrahedron 2001, 57, 3297. (h) Ranu,
B. C.; Mandal, T.; Samanta, S. Org. Lett. 2003, 5, 1439.
(i) Marin, G.; Braga, A. L.; Rosa, A. S.; Galetto, F. Z.;
Burrow, R. A.; Gallardo, H.; Paixao, M. W. Tetrahedron
2009, 65, 4614.
1
3
C NMR (100 MHz, CDCl ): d = 191.7, 139.3, 136.3, 133.8, 130.1,
3
1
28.9, 127.3, 21.3.
Se-4-Tolyl 4-Tolueneselenoate20
Pale light crystals; mp 105–106 °C.
(6) (a) Bhasin, K. K.; Singh, N.; Kumar, R.; Deepali, D. G.;
1
Mehta, S. K.; Klapoetke, T. M.; Crawford, M. J.
H NMR (400 MHz, CDCl ): d = 7.82 (d, J = 8.0 Hz, 2 H), 7.46 (d,
3
J. Organomet. Chem. 2004, 689, 3327. (b) Crich, D.; Grant,
D. J. Org. Chem. 2005, 70, 2384. (c) Andreadou, I.; Menge,
W. M. P. B.; Commandeur, J. N. M.; Worthington, E. A.;
Vermeulen, N. P. E. J. Med. Chem. 1996, 39, 2040.
J = 8.0 Hz, 2 H), 7.27–7.21 (m, 4 H), 2.40 (s, 3 H), 2.38 (s, 3 H).
1
3
C NMR (100 MHz, CDCl ): d = 193.1, 144.8, 139.1, 136.3, 136.0,
3
1
30.2, 129.5, 127.4, 122.2, 21.7, 21.3.
(
d) Sakakibara, M.; Katsumata, K.; Watanabe, Y.; Toru, T.;
Se-4-Tolyl 4-Chlorobenzeneselenoate
Light yellow crystals; mp 94–95 °C (Lit. 95–96 °C).
Ueno, Y. Synthesis 1992, 377.
1
6
(
7) (a) Fukuzawa, S. I.; Niimoto, Y.; Fuiinami, T.; Sakai, S.
Heteroat. Chem. 1990, 6, 491. (b) Zhang, Y.; Yu, Y.; Lin,
R. Synth. Commun. 1993, 23, 189.
8) Zhou, L. H.; Zhang, Y. M. J. Chem. Res., Synop. 1999, 28.
9) Lu, G.; Zhang, Y. Synth. Commun. 1998, 28, 4479.
10) Liu, Y.; K, ; Zhang, Y. Synth. Commun. 1999, 29, 4043.
11) For general reviews, see: (a) Bolm, C.; Legros, J.; Le Paih,
J.; Zani, L. Chem. Rev. 2004, 104, 6217. (b) Fürstner, A.;
Martin, R. Chem. Lett. 2005, 34, 624.
(12) For recent contributions on iron catalysis, see: (a) Fürstner,
A.; Leitner, A.; Méndez, M.; Krause, H. J. Am. Chem. Soc.
2002, 124, 13856. (b) Fürstner, A.; Leitner, A. Angew.
Chem. Int. Ed. 2002, 41, 609. (c) Scheiper, B.;
1
H NMR (400 MHz, CDCl ): d = 7.86 (d, J = 8.8 Hz, 2 H), 7.46–
3
7
.43 (m, 4 H), 7.23 (d, J = 8.0 Hz, 2 H), 2.39 (s, 3 H).
(
(
1
3
C NMR (100 MHz, CDCl ): d = 192.7, 140.2, 139.4, 136.9, 136.2,
3
1
30.3, 129.2, 128.6, 121.8, 21.3.
(
(
Se-n-Butyl Benzeneselenoate
Yellow oil.21
1
H NMR (400 MHz, CDCl ): d = 7.90 (d, J = 8.0 Hz, 2 H), 7.58–
3
7
1
.55 (m, 1 H), 7.46–7.42 (m, 2 H), 3.10 (t, J = 7.2 Hz, 2 H), 1.78–
.70 (m, 2 H), 1.50–1.40 (m, 2 H), 0.95 (t, J = 7.6 Hz, 3 H).
1
3
C NMR (100 MHz, CDCl ): d = 195.0, 139.2, 133.4, 128.7, 127.1,
3
Bonnekessel, M.; Krause, H.; Fürstner, A. J. Org. Chem.
2
3
2.5, 25.5, 23.1, 13.6.
004, 69, 3943. (d) Martin, R.; Fürstner, A. Angew. Chem.
Int. Ed. 2004, 43, 3955. (e) Sapountzis, I.; Lin, W.; Kofink,
C. C.; Despotopoulou, C.; Knochel, P. Angew. Chem. Int.
Ed. 2005, 44, 1654. (f) Kofink, C. C.; Blank, B.; Pagano, S.;
Götz, N.; Knochel, P. Chem. Commun. 2007, 1954.
Acknowledgment
We gratefully acknowledge financial support by the National Natu-
ral Science Foundation of China (Nos. 20972057, 20772043).
(
g) Anilkumar, G.; Bitterlich, B.; Gelalcha, F. G.; Tse, M.
K.; Beller, M. Chem. Commun. 2007, 289. (h) Komeyama,
K.; Morimoto, T.; Takaki, K. Angew. Chem. Int. Ed. 2006,
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Synthesis 2010, No. 7, 1078–1082 © Thieme Stuttgart · New York