Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2009(2): 306-310
DOI: 10.1055/s-0028-1083273
DOI: 10.1055/s-0028-1083273
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Molybdenum(VI) Dichloride Dioxide Catalyzed Conversion of β-Hydroxycarbonyls into α-Bromo 1,3-Dicarbonyls by N-Bromosuccinimide
Further Information
Received
2 September 2008
Publication Date:
12 December 2008 (online)
Publication History
Publication Date:
12 December 2008 (online)
![](https://www.thieme-connect.de/media/synthesis/200902/lookinside/thumbnails/10.1055-s-0028-1083273-1.jpg)
Abstract
A novel and efficient method for the one-pot transformation of β-hydroxycarbonyl compounds to α-brominated 1,3-dicarbonyl compounds is achieved with MoO2Cl2 in the presence of N-bromosuccinimide. All the reactions were carried out under mild conditions and provide good yields of the products. No bromination occurs at benzylic and allylic positions.
Key words
β-hydroxycarbonyl compounds - oxidation - bromination - molybdenum - N-bromosuccinimide
-
1a
Bellina F.Ciucci D.Rossi R.Vergamini P. Tetrahedron 1999, 55: 2103 -
1b
Kel’in AV. Curr. Org. Chem. 2003, 7: 1691 -
1c
Kel’in AV.Maioli A. Curr. Org. Chem. 2003, 7: 1855 -
1d
West AP.Engen DV.Pascal RA. J. Org. Chem. 1992, 57: 784 -
1e
Felix CP.Khatimi N.Laurent AJ. J. Org. Chem. 1995, 60: 3907 -
2a
Katayama S.Fukuda K.Wantanabe T.Yamauchi M. Synthesis 1988, 178 -
2b
Smith AB.Levenberg PA. Synthesis 1981, 567 -
3a
Krapcho AP.Jahngen EGE.Kashdan DS. Tetrahedron Lett. 1974, 15: 2721 -
3b
Rathke MW.Deitch J. Tetrahedron Lett. 1971, 12: 2953 -
3c
Logue MW. J. Org. Chem. 1974, 39: 3455 -
3d
Beck AK.Hoekstra MS.Seebach D. Tetrahedron Lett. 1977, 18: 1187 -
3e
Krapcho AP.Kashdan DS.Jahngen EGE.Lovey AJ. J. Org. Chem. 1977, 42: 1189 -
3f
Staab HA. Angew. Chem., Int. Ed. Engl. 1962, 1: 351 -
3g
Hartzell SL.Rathke MW. Tetrahedron Lett. 1976, 17: 2757 -
4a
Larock RC. Comprehensive Organic Transformations 2nd ed.: VCH Publishers Inc.; New York: 1999. p.715-719 -
4b
Misra AP.Raj K.Bhaduri AP. Synth. Commun. 1999, 29: 3227 -
4c
Coats SJ.Wasserman HH. Tetrahedron Lett. 1995, 36: 7735 -
4d
Yoshida J.Yano S.Ozawa T.Kawabata N. Tetrahedron Lett. 1984, 25: 2817 -
4e
Kaye PT.Meakins GD.Smith AK.Tirel MD. J. Chem. Soc., Perkin Trans. 1 1983, 1677 -
5a
Stotter PL.Hill KA. Tetrahedron Lett. 1972, 13: 4067 -
5b
Khan AT.Ali MA.Goswami P.Choudhury LH. J. Org. Chem. 2006, 71: 8961 -
5c
Curran DP.Bosch E.Kaplan J.Newcomb M. J. Org. Chem. 1989, 54: 1826 -
5d
Tanemura K.Suzuki T.Nishida Y.Satsumabayashi K.Horaguchi T. Chem. Commun. 2004, 470 -
5e
Yang D.Yan Y.-L.Lui B. J. Org. Chem. 2002, 67: 7429 -
5f
Das B.Venkateswarlu K.Mahender G.Mahender I. Tetrahedron Lett. 2005, 46: 3041 -
5g
Meshram HM.Reddy PN.Sadashiv K.Yadav JS. Tetrahedron Lett. 2005, 46: 623 -
6a
Sanz R.Aguado R.Pedrosa MR.Arnáiz FJ. Synthesis 2002, 856 -
6b
Sanz R.Escribano J.Aguado R.Pedrosa MR.Arnáiz FJ. Synthesis 2004, 1629 -
6c
Sanz R.Escribano J.Fernández Y.Aguado R.Pedrosa MR.Arnáiz FJ. Synlett 2005, 1389 -
6d
Chen C.-T.Kuo JH.Pawar VD.Munot YS.Weng SS.Ku CH.Liu CY. J. Org. Chem. 2005, 70: 1188 -
6e
Fernandes AC.Fernandes R.Romao CC.Royo B. Chem. Commun. 2005, 213 -
6f
Weng SS.Lin YD.Chen C.-T. Org. Lett. 2006, 8: 5633 -
6g
Sanz R.Escribano J.Pedrosa MR.Aguado R.Arnáiz FJ. Adv. Synth. Catal. 2007, 349: 713 -
7a
Jeyakumar K.Chand DK. Tetrahedron Lett. 2006, 47: 4573 -
7b
Jeyakumar K.Chand DK. Appl. Organomet. Chem. 2006, 20: 840 -
7c
Jeyakumar K.Chand DK. Synthesis 2008, 807 -
7d
Jeyakumar K.Chand DK. Synthesis 2008, 1685 - 8
Sharma VB.Jain SL.Sain B. J. Mol. Catal. A: Chem. 2005, 227: 47 - 9
Surendra K.Krishnaveni NS.Rao KR. Tetrahedron Lett. 2005, 46: 4111 -
10a
Beignet J.Cox LR. Org. Lett. 2003, 5: 4231 -
10b
Xu C.Yuan C. Tetrahedron 2005, 61: 2169 -
10c
Padhi SK.Chadha A. Synlett 2003, 639 -
10d
Nakamura K.Miyai T.Nozaki K.Ushio K.Oka S.Onho A. Tetrahedron Lett. 1986, 27: 3155 -
10e
Bhandari K.Sharma VL. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43: 2467 -
10f
Chimni SS.Mahajan D. Tetrahedron 2005, 61: 5019 -
10g
Hagiwara H.Inoguchi H.Fukushima M.Hoshi T.Suzuki T. Tetrahedron Lett. 2006, 47: 5371 -
11a
Marigo M.Kumaragurubaran N.Jørgensen KA. Chem. Eur. J. 2004, 10: 2133 -
11b
Salimbeni A.Canevotti R.Paleari F.Bonaccorsi F.Renzetti AR.Belvisi L.Bravi G.Scolastico C. J. Med. Chem. 1994, 37: 3928 - 12
Klosa J. Arch. Pharm. (Weinheim, Ger.) 1953, 286: 391