Subscribe to RSS
DOI: 10.1055/s-2003-42058
An Ionic Liquid Mediated Efficient Oxidation of Alcohols Using o-Iodoxybenzoic Acid (IBX) - a Simple and Eco-friendly Protocol
Publication History
Publication Date:
07 October 2003 (online)
![](https://www.thieme-connect.de/media/synlett/200314/lookinside/thumbnails/10.1055-s-2003-42058-1.jpg)
Abstract
An environmentally benign ionic liquid is shown to be for the first time an excellent medium for mild and selective oxidation of alcohols using IBX at room temperature.
Key words
ionic liquid - hypervalent iodine reagents - selective oxidation - alcohols
-
1a
Varvoglis A. Hypervalent Iodine is Organic Synthesis Academic Press; London: 1997. -
1b
Tohma H.Takizawa S.Maegawa T.Kita Y. Angew. Chem. Int. Ed. 2000, 39: 1306 -
1c
Togo H.Nabona T.Yanaguehi K. J. Org. Chem. 2000, 65: 8391 -
2a
Frigerio M.Santagostino M. Tetrahedron Lett. 1994, 35: 8019 -
2b
Frigerio M.Santagostino M.Sputore S.Palmisano GI. J. Org. Chem. 1995, 60: 7272 -
2c
DeMunari S.Frigerio M.Santagostino M. J. Org. Chem. 1996, 61: 9272 -
2d
Wirth T. Angew. Chem. Int. Ed. 2001, 40: 2812 -
2e
Nicolaou KC.Baran PS.Zhong YL.Barlueng S.Hunt WK.Kranich R.Vega JA. J. Am. Chem. Soc. 2002, 124: 2233 -
2f
Nicolaou KC.Montagnon T.Baran PS.Zhong YL. J. Am. Chem. Soc. 2002, 124: 2245 -
2g
Ozanne A.Pouysegu L.Depernet D.Francois B.Quideau S. Org. Lett. 2003, 5: 2903 -
3a
Dess DB.Martin JC. J. Am. Chem. Soc. 1991, 113: 7277 -
3b
Dess DB.Martin JC. J. Org. Chem. 1983, 48: 4155 -
3c
Meyer SD.Schrieber L. J. Org. Chem. 1994, 59: 7549 -
4a
Moore JD.Finney SN. Org. Lett. 2002, 4: 3001 -
4b
Thattumakara AP.Vinod TK. Tetrahedron Lett. 2002, 43: 569 -
4c
Mulbaier M.Giannis A. Angew. Chem. Int. Ed. 2001, 40: 4393 -
4d
Sorg G.Mengel A.Jung G.Rademann J. Angew. Chem. Int. Ed. 2001, 39: 4395 - 5
Holbrey JD.Seddon KR. Clean Prod. Process. B 1999, 1: 232 -
6a
Welton T. Chem. Rev. 1999, 99: 2071 -
6b
Wasserscheid P.Wilhelm K. Angew. Chem. Int. Ed. 2000, 39: 3772 -
6c
Sheldon R. Chem Commun. 2001, 2399 -
6d
Reynolds JL.Erdner KR.Jones PB. Org. Lett. 2002, 4: 917 -
6e
Ansari IA.Gree R. Org.Lett. 2002, 4: 1507 -
6f
Maya KG.Nearhoof EH.Kiddle JJ. Org.Lett. 2002, 4: 1567 -
6g
Fukuyama T.Shinmen M.Nishitani S.Sato M.Ryu I. Org. Lett. 2002, 4: 1691 -
7a
Fiseher T.Sethi A.Waton T. Tetrahedron Lett. 1999, 40: 793 -
7b
Chiappe C.Capraro D.Conte V.Pieraccini D. Org.Lett. 2001, 3: 1061 -
7c
Handy ST.Zhang X. Org. Lett. 2001, 3: 233 -
7d
Adams CJ.Earle MJ.Roberts G.Seddon KR. Chem Commun. 1998, 2097 -
9a
Kim DH.Jin Y. Bioorg. Med. Chem. Lett. 1999, 9: 691 -
9b
Han Y.Chorev M. J. Org. Chem. 1999, 64: 1972 -
9c
Salvino JM.Mervic M.Mason HJ.Kiesov T.Teager D.Airey J.Labaudiniere R. J. Org. Chem. 1999, 64: 1823 -
9d
Wrodnigg TM.Stuz AE. Angew. Chem. Int. Ed. 1999, 38: 827 -
9e
Steuer S.Ponlech J. Eur. J. Org. Chem. 1999, 1551 -
9f
Kokotos G.Padron JM.Martin T.Gibbons WA.Martin VS. J. Org. Chem. 1998, 63: 3741 -
9g
Armbruster J.Grabowski S.Ruch T.Prinzbach H. Angew. Chem. Int. Ed. 1998, 37: 2242 - 10a Dictonary of Organic Compounds 4th Ed.: Eyre and Spottiswoode Publishers Ltd; London: 1965.
-
10b
Luca LD.Giacomelli G.Porcheddu A. J. Org. Chem. 2001, 66: 7907 -
10c
Castro B.Fehrentz JA. Synthesis 1983, 676 - 12 Contemporarily, the similar work was published by:
Liu Z.Chen Z.-C.Zheng Q.-G. Org. Lett. 2003, 5: 3321
References
Representative Experimental Procedure of Compound 7: To 1 g of molten bmimCl was added 1 mmol of tetrahydro-1-naphthol and 1.2 mmol of IBX and the reaction mixture was stirred at r.t. TLC monitoring shows the completion of reaction in 15 min, after which 10 mL of water was added to the reaction mixture and extracted with EtOAc (3 × 15mL). The organic layer was separated, dried over anhyd Na2SO4, filtered and then evaporated under reduced pressure. The crude product thus obtained was purified by column chromatography (EtOAc/petroleum ether 1:9) to yield 0.133 g (91%) of tetralone.
111H NMR (500 MHz, CDCl3) data of N-Fmoc Valinal: δ = 9.64 (s, 1 H, CHO), 7.78-7.25 (m, 8 H), 5.47 (d, 1 H, J = 7.5 Hz, NH), 4.42-4.33 (m, 3 H, Fmoc-9-H, Fmoc-CH2), 4.23-4.21 (m, 1 H, 2-H), 2.29 (m, 1 H, 3-H), 1.03 [2 d, 6 H, CH(CH3)2, J CH3,3 = 6.9 Hz].