Synlett 2013; 24(1): 90-96
DOI: 10.1055/s-0032-1317676
letter
© Georg Thieme Verlag Stuttgart · New York

Ruthenium Hydride Catalyzed Direct Oxidation of Alcohols to Carboxylic Acids via Transfer Hydrogenation: Styrene Oxide as Oxygen Source

Behjat Barati
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
,
Majid Moghadam*
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
,
Abbas Rahmati*
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
,
Shahram Tangestaninejad
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
,
Valiollah Mirkhani
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
,
Iraj Mohammadpoor-Baltork
Department of Chemistry, Catalysis Division, University of Isfahan, Isfahan 81746-73441, Iran   Fax: +98(311)6689732   Email: moghadamm@sci.ui.ac.ir   Email: a.rahmati@sci.ui.ac.ir
› Author Affiliations
Further Information

Publication History

Received: 07 September 2012

Accepted after revision: 30 October 2012

Publication Date:
05 December 2012 (online)


Abstract

Direct oxidation of alcohols to carboxylic acids using styrene epoxide as oxidant in the presence of [RuHCl(CO)(PPh3)3] complex as catalyst is reported. By this catalytic system, a variety of primary alcohols including substituted benzyl alcohols as well as linear ones were directly converted into carboxylic acids in good to excellent yields.

Supporting Information

 
  • References

    • 1a Transition Metals for Organic Synthesis: Building Blocks and Fine Chemicals. Vol. 1 and 2. Beller M, Bolm C. Wiley-VCH; Weinheim: 1998
    • 1b Davies SG. Organotransition Metal Chemistry: Application to Organic Synthesis. Pergamon Press; Oxford: 1982. Chap. 6
    • 2a Michalak M, Wicha J. Synlett 2005; 2277
    • 2b Doi T, Fukuyama T, Minamino S, Husson G, Ryu I. Chem. Commun. 2006; 1875
    • 2c Krompiec S, Kuznik N, Urbala M, He R. J. Mol. Catal. A: Chem. 2006; 256: 17
    • 2d Doi T, Fukuyama T, Horiguchi J, Okamura T, Ryu I. Synlett 2006; 721
    • 2e Doi T, Fukuyama T, Minamino S, Ryu I. Synlett 2006; 3013
    • 2f Arisawa M, Terada Y, Takahashi K, Nakagawa M, Nishida A. J. Org. Chem. 2006; 71: 4255
    • 2g Burling S, Paine BM, Nama D, Brown VS, Mahon MF, Prior TJ, Pregosin PS, Whittlesey MK, Williams JM. J. J. Am. Chem. Soc. 2007; 129: 1987
    • 2h Casey CP, Clark TB, Guzei A. J. Am. Chem. Soc. 2007; 129: 11821
    • 2i Fukuyama T, Doi T, Minamino S, Omura S, Ryu I. Angew. Chem. Int. Ed. 2007; 46: 5559
    • 2j Omura S, Fukuyama T, Horiguchi J, Murakami Y, Ryu I. J. Am. Chem. Soc. 2008; 130: 14094
    • 2k Shibahara F, Bower JF, Krische MJ. J. Am. Chem. Soc. 2008; 130: 6338
    • 2l Omura S, Fukuyama T, Murakami Y, Okamoto H, Ryu I. Chem. Commun. 2009; 6741
    • 3a Denichoux AI, Fukuyama T, Doi T, Horiguchi J, Ryu I. Org. Lett. 2010; 12: 1
    • 3b Patman RL, Williams VM, Bower JF, Krische MJ. Angew. Chem. Int. Ed. 2008; 47: 5220
    • 4a Wakamatsu H, Nishida M, Adachi N, Mori M. J. Org. Chem. 2000; 65: 3966
    • 4b Krompiec S, Pigulla M, Szczepankiewicz W, Bieg T, Kuznik N, Leszczynska-Sejda K, Kubicki M, Borowiak T. Tetrahedron Lett. 2001; 42: 7095
    • 4c Kuznik N, Krompiec S, Bieg T, Baj S, Skutil K, Chrobok K. J. Organomet. Chem. 2003; 665: 167
    • 4d Shibahara F, Bower JF, Krische MJ. J. Am. Chem. Soc. 2008; 130: 14120
    • 4e Ngai M.-Y, Skucas E, Krische MJ. Org. Lett. 2008; 10: 2705
    • 4f Smejkat T, Han H, Breit B, Krische J. J. Am. Chem. Soc. 2009; 131: 10366
    • 5a Kornievskaja VS, Kruppa AI, Leshina TV. J. Inclusion Phenom. Macrocyclic Chem. 2008; 60: 123
    • 5b Marinello J, Marchand C, Mott BT, Bain A, Thomas CJ, Pommier Y. Biochemistry 2008; 47: 9345
    • 5c Polyakov NE, Leshina TV. Open Conf. Proc. J. 2011; 2: 64
    • 5d Vippagunta SR, Brittain HG, Grant DJ. W. Adv. Drug Delivery Rev. 2001; 48: 3
    • 5e Pierre F, Chua PC, O’Brien SE, Siddiqui-Jain A, Bourbon P, Haddach M, Michaux J, Nagasawa J, Schwaebe MK, Stefan E, Vialettes A, Whitten JP, Chen TK, Darjania L, Stansfield R, Anderes K, Bliesath J, Drygin D, Ho C, Omori M, Proffitt C, Streiner N, Trent K, Rice WG, Ryckman DM. J. Med. Chem. 2011; 54: 635
    • 6a King C. J. Chemtech. 1992; 285
    • 6b Kirk RE, Othmer DF. Encyclopedia of Chemical Technology. 4th ed. Wiley; New York: 1995
    • 6c Hong YK, Hong WH, Han DH. Biotechnol. Bioprocess Eng. 2001; 6: 386
    • 6d Yu L, Lin T, Guo Q, Hao J. Desalination 2003; 154
    • 6e Saito S, Nakasato K, Katoh Y, Oshibe Y, Ishidoya M. Mater. Trans. 2004; 45: 759
    • 6f Wang Z, Luo Y, Yu P. J. Memb. Sci. 2006; 280
    • 6g Ferrer JS. J, Laborie S, Durand G, Rakib M. J. Memb. Sci. 2006; 280
    • 6h Vertova A, Aricci G, Rondinini S, Miglio R, Carnelli L, D’Olimpio P. J. Appl. Electrochem. 2009; 39: 2051
    • 6i Reddy N, Li Y, Yang Y. Biotechnol. Prog. 2009; 25: 139
    • 7a Mannam S, Sekar G. Tetrahedron Lett. 2008; 49: 2457
    • 7b Yasuda K, Ley SV. J. Chem. Soc., Perkin Trans. 1 2002; 1024
    • 7c Donze C, Korovchenko P, Gallezot P, Besson M. Appl. Catal., B 2007; 70: 621
    • 7d Schmidt A.-KC, Stark CB. W. Org. Lett. 2011; 13: 4164

      For selected methodological approaches, see:
    • 8a Hunsen M. Synthesis 2005; 2487
    • 8b Tashino Y, Togo H. Synlett 2004; 2010
    • 8c Travis BR, Sivakumar M, Hollist GO, Borhan B. Org. Lett. 2003; 5: 1031
    • 8d Yasuda K, Ley SV. J. Chem. Soc., Perkin Trans. 1 2002; 1024
    • 8e Mazitschek R, Mülbaier M, Giannis A. Angew. Chem. Int. Ed. 2002; 41: 4059 ; Angew. Chem. 2002, 114, 4216
    • 9a Ahmad N, Levison JJ, Robinson SD, Uttley MF. Inorg. Synth. 1974; 15: 45
    • 9b Levison JJ, Robinson SD. J. Chem. Soc. A 1970; 2947
    • 10a Robinson SD. Inorg. Chem. 1977; 16: 137
    • 10b Ahmad N, Levison JJ, Robinson SD, Utteley MF. Inorg. Synth. 1974; 15: 48
    • 11a Robinson SD, Uttley MF. J. Chem. Soc., Dalton Trans. 1973; 1912
    • 11b Dobson A, Robinson SD. J. Organomet. Chem. 1975; 87: C52
    • 11c Dobson A, Robinson SD, Uttley MF. J. Chem. Soc., Dalton Trans. 1975; 370
    • 11d Dobson A, Robinson SD. Inorg. Chem. 1977; 16: 1321
  • 12 Bianchi M, Matteoli U, Frediani P, Menchi G, Otteghi C, Marchetti M. J. Organomet. Chem. 1983; 252: 317
  • 13 Itoh K, Nagashima H, Ohshima T, Oshima N, Nishiyama H. J. Organomet. Chem. 1984; 272: 179
  • 14 Young R, Wilkinson G. Inorg. Synth. 1977; 17: 75
  • 15 Douglas PG, Shaw BL. J. Chem. Soc. A 1970; 1556
  • 16 Coe BJ, Glenwright S. J. Coord. Chem. Rev. 2000; 203: 5
  • 17 Watanabe Y, Morisaki Y, Kondo T, Mitsudo T. J. Org. Chem. 1996; 61: 4214
  • 18 Kuwahara T, Fukuyama T, Ryu I. Org. Lett. 2012; 14: 4703