RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2003(3): 0408-0412
DOI: 10.1055/s-2003-37343
DOI: 10.1055/s-2003-37343
PAPER
© Georg Thieme Verlag Stuttgart · New York
Solvent-Free and Selective Oxidation of Hydroxy Groups to their Corresponding Carbonyl Functions with Ferric Nitrate Activated by Heteropoly Acids
Weitere Informationen
Received
21 November 2002
Publikationsdatum:
19. Februar 2003 (online)
Publikationsverlauf
Publikationsdatum:
19. Februar 2003 (online)
![](https://www.thieme-connect.de/media/synthesis/200303/lookinside/thumbnails/10.1055-s-2003-37343-1.jpg)
Abstract
Keggin-type heteropoly acids revealed high catalytic activity for swift and selective oxidation of various hydroxy functionalities to the corresponding carbonyl groups using ferric nitrate as an oxidant under mild and solvent-free conditions. We have found that the catalytic activities of the heteropoly acids were much higher than mineral or solid acids such as sulfuric acid, p-toluenesulfonic acid, triflic acid, acidic Amberlyst-15, Montmorillonite-K10 clay, and HY-zeolite.
Key words
alcohols - carbonyl compounds - ferric nitrate - heteropoly acids - oxidations
- 1
Hudlicky M. Oxidations in Organic Chemistry, ACS Monograph 186 ACS; Washington DC: 1990. - 2
Muzart J. Chem. Rev. 1992, 92: 113 -
3a
Mancuso AJ.Swern D. Synthesis 1981, 165 -
3b
Tidwell TT. Synthesis 1990, 857 -
4a
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 -
4b
Dess DB.Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 - 5
Klein WJ. In Organic Syntheses by Oxidation with Metal CompoundsMijs WJ.De Jonge CRHI. Plenum; New York: 1986. -
6a
Okuhara T.Mizuno N.Misono M. Appl. Catal., A 2001, 222: 63 -
6b
Misono M. Chem. Commun. 2001, 1141 -
6c
Kozhevnikov IV. Chem. Rev. 1998, 98: 171 -
6d
Mizuno N.Misono M. Chem. Rev. 1998, 98: 199 -
6e
Okuhara T.Mizuno N.Misono M. Adv. Catal. 1996, 41: 113 -
7a
Ono Y. In Perspective in CatalysisThomas JM.Zamaraev KI. Blackwell; London: 1992. p.431 -
7b
Kozhevnikov IV. Catal. Rev.-Sci. Eng. 1995, 37: 311 -
7c
Okuhara T.Misuno N.Misono M. Adv. Catal. 1996, 41: 113 -
7d
Hill CL.Prosser-McCartha CM. Coord. Chem. Rev. 1995, 143: 407 -
8a
Kozhevnikov IV. Russ. Chem. Rev. 1987, 56: 811 -
8b
Okuhara T.Hu C.Hashimoto M.Misono M. Bull. Chem. Soc. Jpn. 1994, 67: 1186 -
9a
Tiofeeva MN.Dimidov AV.Kozhevnikov IV. J. Mol. Catal. 1993, 79: 21 -
9b
Drago RS.Dias JA.Maier TO. J. Am. Chem. Soc. 1997, 119: 7702 -
9c
Okuhara T.Watanabe H.Nishimura T.Inumaru K.Misono M. Chem. Mater. 2000, 12: 2230 -
10a
Misono M.Ono I.Koyano G.Aoshima A. Pure Appl. Chem. 2000, 72: 1305 -
10b
Misono M. C. R. Acad. Sci. Paris, Ser. IIc, Chim. 2000, 471 -
11a
Firouzabadi H.Iranpoor N.Amani K. Green Chem. 2000, 3: 131 -
11b
Firouzabadi H.Iranpoor N.Amani K. Synthesis 2001, 59 -
11c
Firouzabadi, H.; Iranpoor, N.; Amani, K. J. Mol. Catal. 2002, in print.
-
11d
Firouzabadi H.Iranpoor N.Amani K.Nowrouzi F. J. Chem. Soc., Perkin Trans. 1 2002, 2601 -
12a
Hirano M.Ukawa K.Yakabe S.Morimoto T. Synth. Commun. 1997, 27: 1527 -
12b
Hirano M.Komiya K.Yakabe S.Clark JH.Morimoto T. Org. Prep. Proced. Int. 1996, 28: 705 -
12c
Hirano M.Ukawa K.Yakabe S.Morimoto T. Org. Prep. Proced. Int. 1997, 29: 480 -
12d
Khadilkar B.Borkar S. Synth. Commun. 1998, 28: 207 -
12e
Hirano M.Komiya K.Morimito T. Org. Prep. Proced. Int. 1995, 27: 703 -
12f
Cseri T.Bekassy S.Figueras F. Bull. Soc. Chim. Fr. 1996, 133: 547 -
12g
Figueras F.Bekassy S.Cseri T. New J. Chem. 1996, 20: 357 -
12h
Heravi MM.Ajami D.Mojtahedi MM.Ghassemzadeh M. Tetrahedron Lett. 1999, 40: 561 -
12i
Varma RS.Dahiya R. Tetrahedron Lett. 1998, 39: 1307 -
12k
Laszlo P.Cornelis A. Synthesis 1985, 909 -
12l
Laszlo P.Cornelis A. Synthesis 1980, 849 - 13
Heravi MM.Ajami D.Mojtahedi MM.Ghassemzadeh M. Chem. Commun. 1999, 833 - 14
Misono M.Misono N.Katamura K.Kasai A.Konishi Y.Sakata K.Okuhara T.Yoneda Y. Bull. Chem. Soc. Jpn. 1982, 55: 400 - 15
Misono M.Okuhara T.Nishimura T.Watanabe H. J. Mol. Catal. 1992, 74: 247 - 16
Tsigdinos GA.Hallada CJ. Inorg. Chem. 1968, 7: 437 - 17
Lyon DK.Miller WK.Novet T.Domaille PJ.Evitt E.Johnson DC.Finke RG. J. Am. Chem. Soc. 1991, 113: 7209