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Synlett 2003(12): 1868-1870  
DOI: 10.1055/s-2003-41411
LETTER
© Georg Thieme Verlag Stuttgart · New York

(NO)Ru(salen)-Catalyzed Aerobic Oxidation of o-Hydroxybenzyl Alcohol Derivatives­

Aya Tashiro, Akimasa Mitsuishi, Ryo Irie, Tsutomu Katsuki*
Department of Chemistry, Faculty of Science, Graduate School, Kyushu University 33, CREST, Science and Technology (JST), Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan
Fax: +81(92)6422607; e-Mail: katsuscc@mbox.nc.kyuhsu-u.ac.jp;
Further Information

Publication History

Received 8 July 2003
Publication Date:
28 August 2003 (online)

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Abstract

Various salicylaldehyde derivatives were prepared from the corresponding alcohols in good to excellent yields by ecologically benign aerobic oxidation using ruthenium salen nitrosyl complex 1 as catalyst under visible light-irradiation.

Key words

aerobic oxidation - oxygen - ruthenium salen complex - salicylaldehyde

    References

  • 1a Brunner H. Zettlmeier W. Handbook of Enantioselective Catalysis   Vol. 1:  VCH; Weinheim: 1993. 
    Google Scholar
  • 1b Brunner H. Zettlmeier W. Handbook of Enantioselective Catalysis   Vol. 2:  VCH; Weinheim: 1993. 
    Google Scholar
  • 2a Catalytic Asymmetric Synthesis   2nd ed.:  Ojima I. Wiley-VCH; New York: 2000. 
    Google Scholar
  • 2b Comprehensive Asymmetric Catalysis   Jacobsen EN. Pfaltz A. Yamamoto H. Springer; Berlin: 2000. 
    Google Scholar
  • 3 Katsuki T. Synlett  2003,  281 
    Article in Thieme ConnectGoogle Scholar
  • 4a Fieser LF. Fieser M. In Reagents for Organic Synthesis   Vol. 1:  Wiley and Sons; New York: 1967.  p.215 
    Google Scholar
  • 4b Fieser LF. Fieser M. In Reagents for Organic Synthesis   Vol. 1:  Wiley and Sons; New York: 1967.  p.637 
    Google Scholar
  • 5a Ley SV. Madin A. In Comprehensive Organic Synthesis   Vol. 7:  Trost BM. Fleming I. Pergamon; Oxford: 1991.  p.251 
    Google Scholar
  • 5b Heravi MM. Kiakojoori R. Hydar KT. J. Chem. Research, Synop.  1998,  656 
    Google Scholar
  • 6 Li C. Xu Y. Lu M. Zhao Z. Liu L. Zhao Z. Cui Y. Zheng P. Ji X. Gao G. Synlett  2002,  2041 
    Article in Thieme ConnectGoogle Scholar
  • 7 Krohn K. Khanbabaee K. Rieger H. Chem. Ber.  1990,  123:  1357 
    CrossrefGoogle Scholar
  • 8a Lloyd WG. J. Org. Chem.  1967,  32:  2816 
    CrossrefGoogle Scholar
  • 8b Markó IE. Giles PR. Tsukazaki M. Brown SM. Urch CJ. Science  1996,  274:  2044 
    CrossrefGoogle Scholar
  • 8c Kaneda K. Fujii M. Morioka K. J. Org. Chem.  1996,  61:  4502 
    CrossrefGoogle Scholar
  • 8d Markó IE. Giles PR. Tsukazaki M. Chellé-Regnaut I. Urch CJ. Brown SM. J. Am. Chem. Soc.  1997,  119:  12661 
    CrossrefGoogle Scholar
  • 8e Hanyu A. Takezawa E. Sakaguchi S. Ishii Y. Tetrahedron Lett.  1998,  39:  5557 
    CrossrefGoogle Scholar
  • 8f Nishimura T. Onoue T. Ohe K. Uemura S. J. Org. Chem.  1999,  64:  6750 
    CrossrefGoogle Scholar
  • 8g ten Brink GJ. Arends IWCE. Sheldon RA. Science  2000,  287:  1636 
    CrossrefGoogle Scholar
  • 8h Ishii Y. Sakaguchi S. Iwahama T. Adv. Synth. Catal.  2001,  343:  393 
    CrossrefGoogle Scholar
  • 8i Dijksman A. Marino-González A. iPayeras AM. Arends IWCE. Sheldon RA. J. Am. Chem. Soc.  2001,  123:  6826 
    CrossrefGoogle Scholar
  • 8j Ji H. Mizugaki T. Ebitani K. Kaneda K. Tetrahedron Lett.  2002,  43:  7179 
    CrossrefGoogle Scholar
  • 8k Yamaguchi K. Mizuno N. Angew. Chem. Int. Ed.  2002,  41:  4538 
    CrossrefGoogle Scholar
  • 8l Uozumi Y. Nakano R. Angew. Chem. Int. Ed.  2003,  42:  194 
    CrossrefGoogle Scholar
  • 9a Matsumoto M. Ito S. J. Chem. Soc., Chem. Commun.  1981,  907 
    CrossrefGoogle Scholar
  • 9b Matsumoto M. Watanabe N. J. Org. Chem.  1984,  49:  3435 
    CrossrefGoogle Scholar
  • 9c Kaneda K. Miyoshi T. Imanaka T. J. Mol. Catal.  1991,  64:  L7 
    CrossrefGoogle Scholar
  • 9d Punniyamurthy T. Iqbal J. Tetrahedron Lett.  1994,  35:  4007 
    CrossrefGoogle Scholar
  • 9e Rajendran S. Trivedi DC. Synthesis  1995,  153 
    CrossrefGoogle Scholar
  • 9f Peterson KP. Larock RC. J. Org. Chem.  1998,  63:  3185 
    CrossrefGoogle Scholar
  • 9g Coleman KS. Coppe M. Thomas C. Osborn JA. Tetrahedron Lett.  1999,  40:  3723 
    CrossrefGoogle Scholar
  • 9h Wolfson A. Wuyts S. De Vos DE. Vankelecom IFJ. Jacobs PA. Tetrahedron Lett.  2002,  43:  8107 
    CrossrefGoogle Scholar
  • 10a Capdevielle P. Baranne-Lafont J. Sparfel D. Cuong NK. Maumy M. J. Mol. Catal.  1988,  47:  59 
    Google Scholar
  • 10b Sparfel D. Baranne-Lafont J. Cuong NK. Capdevielle P. Maumy M. Tetrahedron  1990,  46:  793 
    Google Scholar
  • 10c Helene L. inventors; Eur. Pat. Apl. EP  0667331.  ; Chem. Abstr. 1995, 123, 198421
  • 10d Manabe Y, Masuda Y, and Inoe A. inventors; Jpn. Kokai Tokkyo Koho, JP  08245479.  .; Chem. Abstr. 1996, 126, 7818
  • 10e Milone C. Ingoglia R. Neri IG. Pistone A. Galvagno S. Appl. Catal., A.  2001,  211:  251 
    Google Scholar
  • 10f Griffin K. Johnston P. Bennett SC. Kaliq S. Speciality Chemicals Magazine  2001,  13 
    Google Scholar
  • 11 Miyata A. Murakami M. Irie R. Katsuki T. Tetrahedron Lett.  2001,  42:  7067 
    CrossrefGoogle Scholar
  • 12a Hayashi M. Yoshimoto K. Yamada K. Nakayama S. Hayashi H. Yamazaki S. Green Chem.  2000,  2:  257 
    Google Scholar
  • 12b Hayashi M. Yamada K. Hirata N. Tanaka K. Oguni N. Harada K. Matsushita A. Kawachi Y. Sasaki H. Israel J. Chem.  2002,  41:  241 
    Google Scholar
  • The desired aldehyde was obtained in 35% together with 5 in 3%, under usual conditions. In order to minimize the formation of the coupling products, slow addition of 4 to the reaction medium was examined, but the yield of the desired aldehyde was insufficient and irreproducible (27-67%), see:
  • 13a Irie R. Noda K. Ito Y. Matsumoto N. Katsuki T. Tetrahedron Lett.  1990,  31:  7345 
    CrossrefGoogle Scholar
  • 13b Irie R. Noda K. Ito Y. Matsumoto N. Katsuki T. Tetrahedron: Asymmetry  1991,  2:  481 
    CrossrefGoogle Scholar
  • 14a Irie R. Katsuki T. unpublished result  , 
    Google Scholar
  • 14b

    To suppress the undesired coupling, protection of phenolic OH group was needed (ref. [13b] ).
  • 15 Irie R. Masutani K. Katsuki T. Synlett  2000,  1433 
    Article in Thieme ConnectGoogle Scholar