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 2010(21): 3736-3740
DOI: 10.1055/s-0030-1258221
DOI: 10.1055/s-0030-1258221
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Bismuth(III) Oxide Catalyzed Oxidation of Alcohols with tert-Butyl Hydroperoxide
Weitere Informationen
Received
8 July 2010
Publikationsdatum:
17. August 2010 (online)
Publikationsverlauf
Publikationsdatum:
17. August 2010 (online)
![](https://www.thieme-connect.de/media/synthesis/201021/lookinside/thumbnails/10.1055-s-0030-1258221-1.jpg)
Abstract
A variety of aromatic, aliphatic and conjugated alcohols were transformed into the corresponding carboxylic acids and ketones with aq 70% t-BuOOH in the presence of catalytic amounts of bismuth(III) oxide. This method possesses a wide range of capabilities, does not involve cumbersome work-up, exhibits chemoselectivity and proceeds under ambient conditions. The resulting products are obtained in good yields within reasonable time. The overall method is green.
Key words
oxidations - alcohols - Bi2O3 - t-BuOOH - reaction rates
- Supporting Information for this article is available online:
- Supporting Information
-
1a
Hollingworth GJ. In Comprehensive Organic Functional Group Transformations Vol. 5:Katritzky AR.Meth-Cohn O.Rees CW.Pattenden G. Elsevier Science; Oxford: 1995. p.23 -
1b
Hudlicky M. In Oxidations in Organic Chemistry, ACS Monograph Series 186 American Chemical Society; Washington DC: 1990. p.174 -
1c
Larock RC. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd ed.: Wiley; New York: 1999. p.1653 -
1d
Smith MB.March J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 5th ed.: Wiley-Interscience; New York: 2001. p.917-919 -
1e
Sheldon RA.Van Bekkum H. Fine Chemicals through Heterogeneous Catalysis Wiley-VCH; Weinheim: 2001. -
2a
Bowden K.Heilbron IM.Jones ERH.Weedon BCL. J. Chem. Soc. 1946, 39 -
2b
Heilbron I.Jones ERH.Sondheimer F. J. Chem. Soc. 1949, 604 -
2c
Bladon P.Fabian JM.Henbest HB.Koch HP.Wood GW.
J. Chem. Soc. 1951, 2402 -
2d
Curtis RG.Heilbron I.Jones ERH.Woods GF. J. Chem. Soc. 1953, 457 -
2e
Bowers A.Halsall TG.Jones ERH.Lemin AJ. J. Chem. Soc. 1953, 2548 -
2f
Djerassi C.Engle RR.Bowers A. J. Org. Chem. 1956, 21: 1547 - 3
Cainelli G.Cardillo G. Chromium Oxidations in Organic Chemistry Springer; Berlin: 1984. - 4
Benjamin RT.Sivakumar M.Hollist GO.Borhan B. Org. Lett. 2003, 5: 1031 - 5
Nwaukwa SO.Keehn PM. Tetrahedron Lett. 1982, 23: 3131 - 6
Ganem B.Heggs RP.Biloski AJ.Schwartz DR. Tetrahedron Lett. 1980, 21: 685 -
7a
Yamada T.Rhode O.Takai T.Mukaiyama T. Chem. Lett. 1991, 5 -
7b
Bhatia B.Punniyamurthy T.Iqbal J.
J. Org. Chem. 1993, 58: 5518 -
7c
Heaney H. Top. Curr. Chem. 1993, 1: 1 -
7d
Kharata AN.Pendleton P.Badalyan A.Abedini M.Amini MM. J. Mol. Catal. A: Chem. 2001, 175: 277 -
7e
Biella S.Prati L.Rossi M.
J. Mol. Catal. A: Chem. 2003, 197: 207 -
7f
Grill JM.Ogle JW.Miller SA. J. Org. Chem. 2006, 71: 9291 -
7g
Joseph JK.Jain SL.Sain JB. Catal. Commun. 2007, 8: 83 -
7h
Lim M.Yoon CM.An G.Rhee H. Tetrahedron Lett. 2007, 48: 3835 -
7i
Zhou XT.Ji HB.Yuan QL.Xu JC.Pei LX.Wang LF. Chin. Chem. Lett. 2007, 18: 926 -
7j
Sloboda-Rozner D.Neimann K.Neumann R. J. Mol. Catal. A: Chem. 2007, 262: 109 -
7k
Mukhopadhyay C.Datta A. Catal. Commun. 2008, 9: 2588 -
7l
Uyanik M.Ishihara K. Chem. Commun. 2009, 2086 -
8a
Noureldin NA.Donald GL. J. Org. Chem. 1982, 47: 2790 -
8b
Murahashi SI.Naota T.Hirai N. J. Org. Chem. 1993, 58: 7318 -
8c
Sato K.Aoki M.Takagi J.Noyori R. J. Am. Chem. Soc. 1997, 119: 12386 -
8d
Sato K.Takagi J.Aoki M.Noyori R. Tetrahedron Lett. 1998, 39: 7549 -
8e
Betzemeier B.Cavazzini M.Quici S.Knochel P. Tetrahedron Lett. 2000, 41: 4343 -
8f
Hongbing J.Mizugaki T.Ebitani K.Kaneda K. Tetrahedron Lett. 2002, 43: 7179 -
8g
Steinhoff BA.Stahl SS. Org. Lett. 2002, 4: 4179 -
8h
Ten Brink GJ.Arends ICWE.Sheldon RA. Adv. Synth. Catal. 2002, 344: 355 -
8i
Maeda Y.Kakiuchi N.Matsumura S.Nishimura T.Kawamura T.Uemura S. J. Org. Chem. 2002, 67: 6718 -
8j
Yamaguchi K.Mizuno N. Chem. Eur. J. 2003, 9: 4353 -
8k
Sharma VB.Jain SL.Sain B. Tetrahedron Lett. 2003, 44: 383 -
8l
Jeyakumar K.Chand DK. Appl. Organomet. Chem. 2006, 20: 840 -
9a
Miyazawa T.Endo T.Shiihashi S.Okawara M. J. Org. Chem. 1985, 50: 1332 -
9b
Anelli PL.Biffi C.Montanari F.Quici S. J. Org. Chem. 1987, 52: 2559 -
9c
Nooy A.De E J.Besemer AC.Bekkum HV. Synthesis 1996, 1153 -
9d
Rychnovsky SD.Vaidyanathan R. J. Org. Chem. 1999, 64: 310 -
9e
Zhao M.Li J.Song Z.Desmond R.Tschaen DM.Grabowski EJJ.Reider PJ. J. Org. Chem. 1999, 64: 2564 -
9f
Tashino Y.Togo H. Synlett 2004, 2010 - 10
Chakraborty D.Gowda RR.Malik P. Tetrahedron Lett. 2009, 50: 6553 - 11
Malik P.Chakraborty D. Tetrahedron Lett. 2010, 51: 3521 - 12 Encyclopedia of Reagents for Organic Synthesis Vol. 1: Wiley: 2001. p.538
-
13a
Stevens RV.Chapman KT.Stubbs CA.Tam WW.Albizati KF. Tetrahedron Lett. 1982, 23: 4647 -
13b
Wilson SR.Tofigh S.Misra RN. J. Org. Chem. 1982, 47: 1360 -
14a
Bal BS.Childers WE.Pinnick HW. Tetrahedron 1981, 37: 2091 -
14b
Dalcanale E.Montanari F. J. Org. Chem. 1986, 51: 567 -
15a
Ogawa T.Matsui M. J. Am. Chem. Soc. 1976, 98: 1629 -
15b
Cheung Y.-F. Tetrahedron Lett. 1979, 3809