Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York Oxidation of Alcohols with Catalytic Amounts of IBX Agnes Schulze, Athanassios Giannis*Institut für Organische Chemie, Universität Leipzig, Johannisallee 29, 04103 Leipzig, GermanyFax: +49(341)9736599; e-Mail: giannis@uni-leipzig.de; Recommend Article Abstract Buy Article All articles of this category Abstract Herein we present a catalytic IBX-based method for the oxidation of alcohols. Using this system a variety of benzylic alcohols were transformed to aldehydes in good yields whereas secondary alcohols were easily converted to ketones. Primary aliphatic alcohols were oxidised to the corresponding carboxylic acids. 2-Iodobenzoic acid can also be used instead of IBX. Key words alcohols - aldehydes - catalytic oxidation - carboxylic acids - ketones Full Text References References 1a Sheldon RA. Koshi JK. Metal-catalyzed Oxidations of Organic Compounds Academic Press; New York: 1984. 1b Hudlicky M. Oxidations in Organic Chemistry, ACS Monograph 186 ACS; Washington D.C.: 1990. 1c Armstrong A. Synth. Met. 2003, 99: 21 1d Sheldon RA. Arends IWCE. ten Brink GJ. Dijksman A. Acc. Chem. Res. 2002, 35: 774 1e de Nooy AEJ. Besemer AC. Bekkum HV. Synthesis 1996, 1153 2 Kroutil W. Mang H. Edegger K. Faber K. Adv. Synth. Catal. 2004, 346: 125 3 Adam W. Saha-Möller CR. Ganeshpure PA. Chem. Rev. 2001, 101: 3499 4a Frigerio M. Santagostino M. Sputore S. J. Org. Chem. 1999, 64: 4537 4b Frigerio M. Santagostino M. Sputore S. Palmisano G. J. Org. Chem. 1995, 60: 7272 4c Wirth T. Angew. Chem. Int. Ed. 2001, 40: 2812 ; Angew. Chem. 2001, 113, 2893 4d Wirth T. In Organic Synthesis Highlights V Schmalz H.-G. Wirth T. VCH; Weinheim: 2003. p.144 5a Tohma H. Kita Y. Adv. Synth. Catal. 2004, 346: 111 5b Zhdankin VV. Stang PJ. Chem. Rev. 2002, 102: 2523 5c Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997. 5d Wirth T. Top. Curr. Chem. 2003, 224: 185 6 Bolm C. Magnus AS. Hildebrand JP. Org. Lett. 2000, 2: 1173 7a Zhao M. Li J. Mano E. Song Z. Tschaen DM. Grabowski EJJ. Reider PJ. J. Org. Chem. 1999, 64: 2564 7b Anelli PL. Biffi C. Montanari F. Quici S. J. Org. Chem. 1987, 52: 2559 8 Liu R. Liang X. Dong C. Hu X. J. Am. Chem. Soc. 2004, 126: 4112 9 Miller RA. Hoerner RS. Org. Lett. 2003, 5: 285 10 Bjorsvik HR. Liguori L. Constantino F. Minisci F. Org. Process Res. Dev. 2002, 6: 197 11 Plumb JB. Harper DJ. Chem. Eng. News 1990, 68 (July 16): 3 12 Ozanne A. Pouységu L. Depernet D. Francois B. Quideau S. Org. Lett. 2003, 5: 2903 13 Mülbaier M. Giannis A. Angew. Chem. Int. Ed. 2001, 40: 4393 ; Angew. Chem. 2001, 113, 4530 14 Mazitschek R. Mülbaier M. Giannis A. Angew. Chem. Int. Ed. 2002, 41: 4059 ; Angew. Chem. 2002, 114, 4216 15 Schulze A. Giannis A. Adv. Synth. Catal. 2004, 346: 252 16 More JD. Finney NS. Org. Lett. 2002, 4: 3001 17 Trost BM. Braslau R. J. Org. Chem. 1988, 53: 532 18 Travis BR. Sivakumar M. Hollist GO. Borhan B. Org. Lett. 2003, 5: 1031 19 de Munari S. Frigerio M. Santagostino M. J. Org. Chem. 1996, 61: 9272 20 Bartra M. Vilarrasa J. J. Org. Chem. 1991, 56: 5132 21 Wong M.-K. Chung N.-W. He L. Yang D. J. Am. Chem. Soc. 2003, 125: 158 22 Note added in proof: After submission of our manuscript for publication, the following article appeared in the literature: In Situ Generation of o-Iodoxybenzoic Acid (IBX) and the Catalytic Use of It in Oxidation Reactions in the Presence of Oxone as a Co-oxidant: Thottumkara AP. Bowsher MS. Vinod TK. Org. Lett. 2005, 7: 2933