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Synthesis 2010(1): 33-35
DOI: 10.1055/s-0029-1217081
DOI: 10.1055/s-0029-1217081
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Regioselective Hydroxyselenation of Styrenes by Diselenides Using the Zn/AlCl3 System
Further Information
Received
30 July 2009
Publication Date:
26 October 2009 (online)
Publication History
Publication Date:
26 October 2009 (online)
Abstract
A facile, zinc/aluminum(III) chloride promoted highly regioselective one-pot procedure has been developed for the preparation of β-hydroxy selenides from various styrenes and diselenides by Se-Se bond cleavage using the Zn/AlCl3 system in aqueous acetonitrile and in the presence of oxygen.
Key words
β-hydroxy selenides - diselenides - styrenes - regioselective - Zn/AlCl3 system
-
1a
Sharpless KB.Lauer RF. J. Am. Chem. Soc. 1973, 95: 2697 -
1b
Dumont W.Bayet P.Krief A. Angew. Chem., Int. Ed. Engl. 1974, 13: 804 -
1c
Seebach D.Beck AK. Angew. Chem., Int. Ed. Engl. 1974, 13: 805 - 2
Hori T.Sharpless KB. J. Org. Chem. 1978, 43: 1689 - 3
Remion J.Dumont W.Krief A. Tetrahedron Lett. 1976, 17: 1385 - 4
Leonard-Coppens AM.Krief A. Tetrahedron Lett. 1976, 17: 3227 - 5
Reich HJ.Chow F. J. Chem. Soc., Chem. Commun. 1975, 790 - 6
Dumont W.Krief A. Angew. Chem., Int. Ed. Engl. 1975, 14: 350 - 7
Sevrin M.Dumont W.Hevesi L.Krief A. Tetrahedron Lett. 1976, 17: 2647 -
8a
Gruttadauria M.Aprile C.Riela S.Noto R. Tetrahedron Lett. 2001, 42: 2213 -
8b
Gruttadauria M.Lo Meo P.Noto R. Tetrahedron 2001, 57: 1819 -
8c
Gruttadauria M.Lo Meo P.Noto R. Tetrahedron 1999, 55: 14097 -
8d
Gruttadauria M.Lo Meo P.Noto R. Tetrahedron 1999, 55: 4769 -
8e
Gruttadauria M.Lo Meo P.Noto R. Tetrahedron Lett. 1999, 40: 8477 -
9a
Kametani T.Suzuki K.Kurobe H.Nemoto H. Chem. Pharm. Bull. 1981, 29: 105 -
9b
Kametani T.Kurobe H.Nemoto H. J. Chem. Soc., Perkin Trans. 1 1981, 756 - 10
Toshimitsu A.Hayashi G.Terao K.Vemura S. J. Chem. Soc., Perkin Trans. 1 1986, 343 -
11a
Movassagh B.Shamsipoor M. Synlett 2005, 1316 -
11b
Das B.Saidi Reddy V.Ramu R. J. Mol. Catal. A: Chem. 2007, 263: 276 -
11c
de Rego Barros OS.de Carvalho AB.Lang ES.Peppe C. Lett. Org. Chem. 2004, 1: 43 -
11d
Sridhar R.Srinivas B.Surendra K.Krishnaveni NS.Rao KR. Tetrahedron Lett. 2005, 46: 8837 -
11e
Cravador A.Krief A. Tetrahedron Lett. 1981, 22: 2491 -
11f
Dowsland J.McKerlie F.Procter DJ. Tetrahedron Lett. 2000, 41: 4923 -
11g
Sakakibara M.Katsumata K.Watanabe Y.Toru T.Ueno Y. Synthesis 1992, 377 -
12a
Wirth T.Fragale G.Spichty M. J. Am. Chem. Soc. 1998, 120: 3376 -
12b
Toshimitsu A.Aoai T.Owada H.Uemura S.Okano M. Tetrahedron 1985, 41: 5301 -
12c
Denis JN.Vicens J.Krief A. Tetrahedron Lett. 1979, 20: 2697 -
12d
Nicolaou KC.Claremon DA.Barnette WE.Seitz SP. J. Am. Chem. Soc. 1979, 101: 3704 -
12e
Reich HJ. J. Org. Chem. 1974, 39: 428 - 13
Zhang W.Yu H.Gao Y.Meng J.Mutsuura T. Chem. Commun. 2003, 498 - 14
Movassagh B.Navidi M. Tetrahedron Lett. 2008, 49: 6712 - 15
Surendra K.Krishnaveni NS.Sridhar R.Rao KR. J. Org. Chem. 2006, 71: 5819 -
16a
Chen X.Wu H.Su W.Xu R.Liu M.Ding J. J. Chem. Res. 2007, 325 -
16b
Uemura S.Ohe K.Sugita N. J. Chem. Soc., Chem. Commun. 1988, 111