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-00000083.xml
Synlett 2014; 25(20): 2923-2927
DOI: 10.1055/s-0034-1378913
DOI: 10.1055/s-0034-1378913
letter
TEMPO/NBu4Br-Catalyzed Selective Alcohol Oxidation with Periodic Acid
Weitere Informationen
Publikationsverlauf
Received: 15. September 2014
Accepted: 02. Oktober 2014
Publikationsdatum:
29. Oktober 2014 (online)
Abstract
Oxidation of primary and secondary alcohols, using catalytic amounts of TEMPO and tetra-n-butylammonium bromide in combination with periodic acid and wet alumina in dichloromethane is described. This oxidizing system is compatible with a broad range of functional groups and acid-sensitive protecting groups. Chemoselective oxidation of secondary alcohols in the presence of primary alcohols was observed.
-
References and Notes
- 1a Sheldon RA, Kochi JK. Metal-Catalyzed Oxidation of Organic Compounds . Academic Press; New York: 1982
- 1b Hudlicky M. Oxidations in Organic Chemistry . ACS; Washington, DC: 1990
- 2a Cainelli G, Cardillo G. Chromium Oxidations in Organic Chemistry . Springer; New York: 1984
- 2b Luzzio FA. Org. React. 1998; 53: 1
- 3a Fatiadi AJ. Synthesis 1976; 65
- 3b Fatiadi AJ. Synthesis 1976; 133
- 3c Fatiadi AJ. Synthesis 1987; 85
- 4a Mancuso AJ, Swern D. Synthesis 1981; 165
- 4b Tidwell TT. Synthesis 1990; 857
- 4c Tidwell TT. Org. React. 1990; 39: 297
- 5 For a recent review, see: Tohma H, Kita Y. Adv. Synth. Catal. 2004; 346: 111
- 6 Dess DB, Martin JC. J. Org. Chem. 1983; 48: 4155
- 7 Frigerio M, Santagostino M, Sputore S, Palmisano G. J. Org. Chem. 1995; 60: 7272
- 8a Bobbitt JM, Flores MC. L. Heterocycles 1988; 27: 509
- 8b Yamaguchi M, Miyazawa T, Takata T, Endo T. Pure Appl. Chem. 1990; 62: 217
- 8c de Nooy AE. J, Besemer AC, Van Bekkum HV. Synthesis 1996; 1153
- 8d Adam W, Saha-Möller CR, Ganseshpure PA. Chem. Rev. 2001; 3499
- 8e Sheldon RA, Arends IW. C. E, Ten Brink G.-J, Dijksman A. Acc. Chem. Res. 2002; 35: 774
- 8f Bobbitt JM, Brückner C, Merbouh N. Org. React. 2010; 74: 103
- 9a Miyazama T, Endo T, Shiihashi S, Okawara M. J. Org. Chem. 1985; 50: 1332
- 9b Bjørsvih H.-R, Liguori L, Costantino F, Minisci F. Org. Process Res. Dev. 2002; 6: 197
- 9c Miller RA, Hoerrner RS. Org. Lett. 2003; 5: 285
- 9d Liu R, Liang X, Dong C, Hu X. J. Am. Chem. Soc. 2004; 126: 4112
- 9e Anelli PL, Biffi C, Montanari F, Quici S. J. Org. Chem. 1987; 52: 2559
- 9f Anelli PL, Banfi S, Montanari F, Quici S. J. Org. Chem. 1989; 54: 2970
- 9g Siedlecka R, Skarzewski J, Mlochowski J. Tetrahedron Lett. 1990; 31: 2177
- 9h Bolm C, Fey T. Chem. Commun. 1999; 1795
- 9i Dijksman A, Arends IW. C. E, Sheldon RA. Chem. Commun. 2000; 271
- 9j Einhorn J, Einhorn C, Ratajczak F, Pierre J.-L. J. Org. Chem. 1996; 61: 7452
- 9k Inokuchi T, Matsumoto S, Nishiyama T, Torii S. J. Org. Chem. 1990; 55: 462
- 9l Zhao M, Li J, Mano E, Song Z, Tschaen DM, Grabowski EJ. J, Reider PJ. J. Org. Chem. 1999; 64: 2564
- 9m De Luca L, Giacomelli G, Porcheddu A. Org. Lett. 2001; 3: 3041
- 9n De Lucca L, Giacomelli G, Masala S, Porcheddu A. J. Org. Chem. 2003; 68: 4999
- 10a Cella JA, Kelley JA, Kenhan EF. J. Org. Chem. 1975; 40: 1860
- 10b Ganem B. J. Org. Chem. 1975; 40: 1998
- 10c Rychnovski SD, Vaidyanathan R. J. Org. Chem. 1999; 64: 310
- 10d Bolm C, Magnus AS, Hildebrand JP. Org. Lett. 2000; 2: 1173
- 11a De Mico A, Margarita R, Parlanti L, Vescovi A, Piancatelli G. J. Org. Chem. 1997; 62: 6974
- 11b Epp JB, Widlanski TS. J. Org. Chem. 1999; 64: 293
- 11c Sakuratani K, Togo H. Synthesis 2003; 21
- 11d Van Der Bos LJ, Litjens RE. J. N, Van den Berg RJ. B. H. N, Overkleeft HS, Van der Marel GA. Org. Lett. 2005; 7: 2007
- 12 Vatèle J.-M. Synlett 2014; 25: 115
- 13a Vatèle J.-M. Tetrahedron Lett. 2006; 47: 715
- 13b Vatèle J.-M. Synlett 2006; 2055
- 13c Vatèle J.-M. Synlett 2008; 1785
- 13d Vatèle J.-M. Synlett 2009; 2143
- 13e Vatèle J.-M. Tetrahedron 2010; 66: 904
- 13f Barnych B, Vatèle J.-M. Synlett 2011; 2048
- 13g Vatèle J.-M. Synlett 2014; 25: 1275
- 14 Lei M, Hu R.-J, Wang Y.-G. Tetrahedron 2006; 62: 8928
- 15 Kim SS, Nehru C. Synlett 2002; 616
- 16a Hirano M, Oose M, Morimoto T. Bull. Chem. Soc. Jpn. 1991; 64: 1046
- 16b Hirano M, Oose M, Morimoto T. Chem. Lett. 1991; 331
- 16c Greenhalgh RP. Synlett 1992; 235
- 16d Ceccherelli P, Curini M, Marcotullio MC, Epifano F, Rosati O. Synlett 1996; 767
- 17 For a study on the mechanism of Al2O3-catalyzed oxidation, see: Kropp PJ, Breton GW, Fields JD, Tung JC, Loomis BR. J. Am. Chem. Soc. 2000; 122: 4280
- 18 Alcohol oxidation with periodic acid and catalytic bromide anion has been described: Zolfigol MA, Shirini F, Chehardoli G, Kolvari E. J. Mol. Catal. A: Chem. 2007; 265: 272
- 19 Appropriate physical and analytical data were obtained for all new compounds.
- 20 Typical Procedure for the Oxidation of Alcohols (Table 2, Entry 21) Wet alumina was prepared by mixing neutral alumina (50 g, Fluka ref 06300; Brockmann activity 1) with H2O (10 g) and shaking until a free-flowing homogeneous powder was obtained. To a solution of 3-methylhexane-1,3-diol (20a, 0.132 g, 1 mmol) in CH2Cl2 (3 mL) were successively added TEMPO (7.8 mg, 5 mol%), wet alumina (0.913 g), TBAB (16 mg, 5 mol%), and H5IO6 (0.274 g, 1.2 equiv). The brownish suspension was stirred for 5 h at r.t., filtered, and the filtrate was washed with sat. Na2S2O3 aq solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by chromatography on silica gel (PE–Et2O, 1:2) to give the hydroxyaldehyde 20b as a liquid (94 mg, 72%). 1H NMR (300 MHz, C6D6): δ = 9.57 (t, J = 2.3 Hz, 1 H), 2.43 (s, 1 H), 2.14 (dd, J = 15.8, 2.4 Hz, 1 H), 2.04 (dd, J = 15.8, 2.4 Hz, 1 H), 1.32–1.09 (m, 4 H), 1.02 (s, 3 H), 0.8 (t, J = 7.1 Hz, 3 H). 13C NMR (75 MHz, C6D6): δ = 202.6, 71.5, 54.2, 45.3, 27.3, 17.3, 14.6. ESI-HRMS: m/z [M – H]– calcd for C7H13O2: 129.0916; found: 129.0918.
- 21a Shibuya M, Tomizawa M, Suzuki I, Iwabuchi Y. J. Am. Chem. Soc. 2006; 128: 8412
- 21b Lauber MB, Stahl SS. ACS Catal. 2013; 3: 2612
- 21c Holan M, Jahn U. Org. Lett. 2014; 16: 58
- 22 For a review on AZADO and its derivatives, see: Iwabuchi Y. Chem. Pharm. Bull. 2013; 61: 1197
- 23a Anderson JC, McDermott BP, Griffin EJ. Tetrahedron 2000; 56: 8747
- 23b Avi M, Gaisberger R, Feichtenhofer S, Griengl H. Tetrahedron 2009; 65: 5418
- 24a Semmelhack MF, Chou CS, Cortes DA. J. Am. Chem. Soc. 1983; 105: 4492
- 24b Semmelhack MF, Schmid CR, Cortes DA, Chou CS. J. Am. Chem. Soc. 1984; 106: 3374
- 24c Shibuya M, Tomizawa M, Sasano Y, Iwabuchi Y. J. Org. Chem. 2009; 74: 4619
- 24d Hoover JM, Stahl SS. J. Am. Chem. Soc. 2011; 133: 16901
- 25 Zhao X.-F, Zhang C. Synthesis 2007; 551
- 26 For a review on the chemoselective oxidation of secondary alcohols, see: Arterburn JB. Tetrahedron 2001; 57: 9765
- 27 Bailey WF, Bobbitt JM, Wiberg KB. J. Org. Chem. 2007; 72: 4504
For reviews of TEMPO-catalyzed alcohol oxidation, see:
Halogen-based reagents. For X2, see:
Bleach:
NCS:
NaBrO2:
NaClO2:
Trichloroisocyanuric acid:
Examples of other reoxidants for TEMPO. For MCPBA, see:
Oxone:
For examples of wet alumina mediated oxidations, see: