Efficient CuCl-Catalyzed Selective and Direct Oxidation of β- and γ-Substituted Aliphatic Primary Alcohols to Carboxylic Acids

REFERENCES

• (a) Sheldon , R. A. ; Kochi , J. K. Metal-Catalysed Oxidations of Organic Compounds ; Academic Press , New York , 1981 ; (b) De Nooy , A. E. J. ; Basemer , A. C. ; Bekkum , H. V. On the use of stable organic nitroxyl radicals for the oxidation of primary and secondary alcohols. Synthesis 1996, 1153–1174; (c) March, J. Advanced Organic Chemistry: Reaction, Mechanisms, and Structure, 4th ed.; John Wiley & Sons: New York, 1992.
   Google Scholar
• (a) Ley , S. V. ; J. Norman , J. ; Griffith , W. P. ; Marsden , S. P. Tetraisopropylammonium perruthenate Pr4N+ , TPAP: A catalytic oxidant for organic synthesis . Synthesis 1994 , 639 – 666 ; (b) Murahashi , S. I. ; Naota , T. ; Oda , Y. ; N. Hirai , N. Ruthenium-catalyzed oxidation of alcohols with peracids . Synlett 1995 , 733 – 734 .
   Google Scholar
• (a) Sheldon , R. A. In Dioxygen Activation and Homogeneous Catalytic Oxidation ; L. L. Simandi (Ed.); Elsevier : Amsterdam , 1991 ; p. 573 ; (b) Strukul , G. In Catalytic Oxidations with Hydrogen Peroxide as Oxidant ; Kluwer Academic : London , 1992 ; (c) Sato , K. ; Takagi , J. ; Aoki , M. ; Noyori , R. Hydrogen peroxide oxidation of benzylic alcohols to benzaldehydes and benzoic acids under halide-free conditions. Tetrahedron Lett. 1998, 39, 7549–7552 ; (d) Sato , K. ; Aoki , M. ; Noyori , R. A “Green” route to adipicacid: Direct oxidation of cyclohexenes with 30% hydrogen peroxide. Science 1998, 281, 1646–1647 .
   Google Scholar
• Montanari , E. ; Mulbaier , M. Selective oxidation of aldehydes to carboxylic acids with sodium chlorite–hydrogen peroxide . J. Org. Chem. 1986 , 51 , 567 – 569 .
   Google Scholar
• Corey , E. J. ; Schmidt , G. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic medium . Tetrahedron Lett. 1979 , 20 , 399 – 402 .
   Google Scholar
• (a) Zhao , M. ; Li , J. ; Song , Z. ; Desmond , R. ; Tschaen , D. M. ; Grabowski , E. J. J. ; Reider , P. J. A novel chromium trioxide–catalyzed oxidation of primary alcohols to the carboxylic acids . Tetrahedron Lett. 1998 , 39 , 5323 – 5326 ; (b) Carlsen , P. H. J. ; Katsuki , T. ; Martin , V. S. ; Sharpless , K. B. A greatly improved procedure for ruthenium tetroxide–catalyzed oxidations of organic compounds . J. Org. Chem. 1981 , 46 , 3936 – 3938 ; (c) Mazitschek , R. ; Mulbaier , M. ; Giannis , A. IBX-mediated oxidation of primary alcohols and aldehydes to form carboxylic acids . Angew. Chem. Int. Ed. 2002 , 41 , 4059 – 4061 .
   Google Scholar
• (a) Zhao , M. ; Li , J. ; Mano , E. ; Song , Z. ; Tschaen , D. M. ; Grabowski , E. J. J. ; Reider , P. J. Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach . J. Org. Chem. 1999 , 64 , 2564 ; (b) Anelli , P. L. ; Biffi , C. ; Montanari , C. F. ; Quici , S. Fast and selective oxidation of primary alcohols to aldehydes or carboxylic acids and secondary alcohols to ketones mediated by oxammonium salts under two phase conditions . J. Org. Chem. 1987 , 52 , 2559 – 2562 .
   Web of Science ®Google Scholar
• (a) Bowden , K. ; Heilbron , I. M. ; Jones , E. R. H. ; Weedon , B. C. K. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols . J. Chem. Soc. 1946 , 39 – 45 ; (b) Oehlschlager , A. C. ; Wong , J. W. Synthesis of two macrolide aggregation pheromones from the flat grain beetle, Cryptolestes pusillus (Schoenherr) . J. Org. Chem. 1983 , 48 , 4404 – 4406 .
   Google Scholar
• Berkowitz , L. M. ; Rylander , P. N. Use of ruthenium tetroxide as a multi-purpose oxidant . J. Am. Chem. Soc. 1958 , 80 , 6682 – 6684 .
   Web of Science ®Google Scholar
• Varma , R. S. ; Hogan , M. E. Ruthenium tetraoxide–catalyzed oxidation of nucleosides: A facile synthesis of 5′-carboxylic acid derivatives . Tetrahedron Lett. 1992 , 33 , 7719 – 7720 .
   Web of Science ®Google Scholar
• Murahashi , S. I. ; Naota , T. ; Hirai , N. Aerobic oxidation of alcohols with ruthenium–cobalt bimetallic catalyst in the presence of aldehydes . J. Org. Chem. 1993 , 58 , 7318 – 7319 .
   Web of Science ®Google Scholar
• Noureldin , N. A. ; Donald , G. L. Heterogeneous permanganate oxidations: Oxidation of alcohols using solid hydrated copper permanganate . J. Org. Chem. 1982 , 47 , 2790 – 2792 .
   Web of Science ®Google Scholar
• (a) Strukul , G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant ; Kluwer : Dordrecht , the Netherlands , 1992 ; (b) Sato , K. ; Aoki , M. ; Ogawa , M. ; Hashimoto , T. ; Noyori , R. A practical method for epoxidation of terminal olefins with 30% hydrogen peroxide under halide-free conditions. J. Org. Chem. 1996, 61, 8310–8311 .
   Google Scholar
• (a) Jacobson , S. E. ; Muccigrosso , D. A. ; Mares , F. Oxidation of alcohols by molybdenum and tungsten peroxo complexes . J. Org. Chem. 1979 , 44 , 921 – 924 ; (b) Trost , B. M. ; Masuyama , Y. Chemoselectivity in molybdenum-catalyzed alcohol and aldehyde oxidations . Tetrahedron Lett. 1984 , 25 , 173 – 176 .
   Web of Science ®Google Scholar
• Shulpin , G. B. ; Suus Fink , G. ; Shulpina , L. S. Oxidations by the system hydrogen peroxide–manganese(IV) complex–carboxylic acid, part 3: Oxygenation of ethane, higher alkanes, alcohols, olefins, and sulfides . J. Mol. Catal. A: Chem. 2001 , 170 , 17 – 34 .
   Google Scholar
• (a) Kolthoff , I. M. ; Medalia , A. I. The reaction between ferrous iron and peroxides: Reaction with hydrogen peroxide in the absence of oxygen . J. Am. Chem. Soc. 1949 , 71 , 3777 – 3788 ; (b) Martin , S. E. ; Garrone , A. Efficient solvent-free iron(III)-catalyzed oxidation of alcohols by hydrogen peroxide . Tetrahedron Lett. 2003 , 44 , 549 – 551 ; (c) Barton , D. H. R. ; Beviere , S. D. ; Chabot , B. M. ; Chavasiri , W. ; Taylor , D. K. Studies on the oxidation of alcohols employing t-butyl hydroperoxide (TBHP) and Fe(III) catalysts . Tetrahedron Lett. 1994 , 35 , 4681 – 4684 .
   Web of Science ®Google Scholar
• (a) Sato , K. ; Aoki , M. ; Tagaki , J. ; Noyori , R. Organic solvent and halide-free oxidation of alcohols with aqueous hydrogen peroxide . J. Am. Chem. Soc. 1997 , 119 , 12386 – 12387 ; (b) Venturello , C. ; Gambaro , M. Selective oxidation of alcohols and aldehydes with hydrogen peroxide catalyzed by methyltrioctylammonium tetrakis(oxodiperoxotungsto)phosphate-3 under two-phase conditions . J. Org. Chem. 1991 , 56 , 5924 – 5931 .
   Web of Science ®Google Scholar
• (a) Rothenberg , G. ; Feldberg , L. ; Wiener , H. ; Sasson , Y. Copper-catalyzed homolytic and heterolytic benzylic and allylic oxidation using tert-butyl hydroperoxide . J. Chem. Soc., Perkin Trans. 2 1998 , 2429 – 2434 ; (b) Marko , I. E. ; Gautier , A. ; Dumeunier , R. ; Doda , K. ; Philippart , F. ; Brown , S. M. ; Christopher , J. U. Efficient, copper-catalyzed, aerobic oxidation of primary alcohols . Angew. Chem. Int. Ed. 2004 , 43 , 1588 – 1591 ; (c) Ferguson , G. ; Ajjou , A. N. Solvent-free oxidation of alcohols by t-butyl hydroperoxide catalyzed by water-soluble copper complex . Tetrahedron Lett. 2003 , 44 , 9139 – 9142 ; (d) Boudreau , J. ; Doucette , M. ; Ajjou , A. N. A new and highly efficient water-soluble copper complex for the oxidation of secondary 1-heteroaryl alcohols by tert-butyl hydroperoxide . Tetrahedron Lett. 2006 , 47 , 1695 – 1698 .
   Google Scholar
• (a) Punniyamurthy , T. ; Das , S. Cobalt(II)-catalyzed oxidation of alcohols into carboxylic acids and ketones with hydrogen peroxide. Tetraheron Lett. 2003, 44, 6033–6035; (b) Punniyamurthy , T. ; Das , S. Copper(II)-catalyzed oxidation of alcohols to carbonyl compounds with hydrogen peroxide. Eur. J. Org. Chem. 2003, 3913–3915.
   Google Scholar
• Lei , Z. ; Yan , P. ; Yang , Y. A simple and efficient oxidation system for the oxidation of alcohols utilizing oxone as oxidant catalyzed by polymer-supported 2-iodobenzamide . Catal. Lett. 2007 , 118 , 69 – 71 .
   Google Scholar
• Ragauskas , A. J. ; Jiang , N. Selective aerobic oxidation of activated alcohols into acids or aldehydes in ionic liquids . J. Org. Chem. 2007 , 72 , 7030 – 7033 .
   Google Scholar
• (a) Sreedevi , M. ; Alamsetti , S. K. ; Sekar , G. Aerobic, chemoselective oxidation of alcohols to carbonyl compounds catalyzed by DABCO–copper complex under mild conditions . Adv. Synth. Catal. 2007 , 349 , 2253 – 2257 ; (b) Kumar , S. A. ; Mannam , S. ; Muthupandi , P. ; Sekar , G. Galactose oxidase model: Biomimetic enantiomer-differentiating oxidation of alcohols by a chiral copper complex . Chem. Eur. J. 2009 , 15 , 1086 – 1090 ; (c) Sreedevi , M. ; Sekar , G. CuCl-catalyzed oxidation of aldehydes to carboxylic acids with aqueous tert-butyl hydroperoxide under mild conditions . Tetrahedron Lett. 2008 , 49 , 1083 – 1086 .
   Google Scholar
• Sreedevi , M. ; Sekar , G. CuCl-catalyzed selective oxidation of primary alcohols to carboxylic acids with tert-butyl hydroperoxide at room temperature . Tetrahedron Lett. 2008 , 48 , 2457 – 2460 .
   Google Scholar