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2012 | 1 | 9-11
Article title

Selective Oxidation of Alcohols Catalyzed by a Hemicryptophane-Ruthenium Complex

Content
Title variants
Languages of publication
EN
Abstracts
EN
Hemicryptophane, a covalent molecular capsule that is composed of a cyclotriveratrylene (CTV) host unit, a tris(2-aminoethyl)amine (tren) ligand, and three rigid phenyl spacers, is a useful ligand for preparing synthetic transition metal complexes containing well-defined cavities that mimic the active sites of metalloenzymes. A method for the selective oxidation of primary alcohols using 5 mol % hemicryptophane-ruthenium(II) dichloride as the catalyst and cerium(IV) ammonium nitrate (CAN) as the terminal oxidant is described. The corresponding aldehydes of both benzylic and aliphatic alcohols are afforded in good to excellent yields under mild conditions without significant over-oxidation to produce the corresponding carboxylic acids.
Publisher
Year
Volume
1
Pages
9-11
Physical description
Dates
online
21 - 8 - 2012
accepted
25 - 7 - 2012
received
30 - 6 - 2012
References
  • A. J. Kirby, Angew. Chem., Int. Ed. Engl., 35, 706, (1996)
  • M. Garcia-Viloca, J. Gao, M. Karplus, D. G. Truhlar, Science, 303, 186, (2004)
  • D. Ringe, G. A. Petsko, Science, 320, 1428, (2008)
  • P. W. N. M. van Leeuwen, Supramolecular Catalysis, (Wiley-VCH, Weinheim, 2008)
  • T. S. Koblenz, J. Wassenaar, J. N. H. Reek, Chem. Soc. Rev., 37, 247, (2008)
  • T. Brotin, J.-P. Dutasta, Chem. Rev., 109, 88, (2009)
  • M. Yoshizawa, J. K. Klosterman, M. Fujita, Angew. Chem. Int. Ed., 48, 3418, (2009)
  • S. Richeter, J. Rebek, Jr., J. Am. Chem. Soc., 126, 16280, (2004)
  • M. J. Wilkinson, P. W. N. M. van Leeuwen, J. N. H. Reek, Org. Biomol. Chem., 3, 2371, (2005)
  • T. S. Koblenz, H. L. Dekker, C. G. de Koster, P. W. N. M. van Leeuwen, J. N. H. Reek, Chem. Commun., 1700, (2006)
  • M. Kuil, T. Soltner, P. W. N. M. van Leeuwen, J. N. H. Reek, J. Am. Chem. Soc., 128, 11344, (2006)
  • D. H. Leung, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc., 128, 9781, (2006)
  • T. Hasegawa, Y. Furusho, H. Katagiri, E. Yashima, Angew. Chem. Int. Ed., 46, 5885, (2007)
  • D. H. Leung, R. G. Bergman, K. N. Raymond, J. Am. Chem. Soc., 129, 2746, (2007)
  • I. Gosse, J.-P. Dutasta, M. Perrin, A. Thozet, New J. Chem., 23, 545, (1999)
  • A. Gautier, J.-C. Mulatier, J. Crassous, J.-P. Dutasta, Org. Lett., 7, 1207, (2005)
  • A. Martinez, J.-P. Dutasta, J. Catal., 267, 188, (2009)
  • A. Martinez, L. Guy, J.-P. Dutasta, J. Am. Chem. Soc., 132, 16733, (2010)
  • A. Martinez, V. Robert, H. Gornitzka, J.-P. Dutasta, Chem. Eur. J., 16, 520, (2010)
  • O. Perraud, P. D. Raytchev, A. Martinez, J.-P. Dutasta, Chirality, 22, 885, (2010)[PubMed]
  • P. D. Raytchev, O. Perraud, C. Aronica, A. Martinez, J.-P. Dutasta, J. Org. Chem., 75, 2099, (2010)
  • B. Chatelet, E. Payet, O. Perraud, P. Dimitrov-Raytchev, L. L. Chapellet, V. Dufaud, A. Martinez, J.-P. Dutasta, Org. Lett., 13, 3706, (2011)
  • N. S. Khan, J. M. Perez-Aguilar, T. Kaufmann, P. A. Hill, O. Taratula, O.-S. Lee, P. J. Carroll, J. G. Saven, I. J. Dmochowski, J. Org. Chem., 76, 1418, (2011)
  • L. Wang, G.-T. Wang, X. Zhao, X.-K. Jiang, Z.-T. Li, J. Org. Chem., 76, 3531, (2011)
  • O. Perraud, A. Martinez, J.-P. Dutasta, Chem. Commun., 47, 5861, (2011)
  • O. Perraud, V. Robert, A. Martinez, J.-P. Dutasta, Chem. Eur. J., 17, 4177, (2011)
  • P. D. Raytchev, A. Martinez, H. Gornitzka, J.-P. Dutasta, J. Am. Chem. Soc., 133, 2157, (2011)
  • O. Perraud, S. Lefevre, V. Robert, A. Martinez, J.P. Dutasta, Org. Biomol. Chem., 10, 1056, (2012)
  • O. Perraud, V. Robert, H. Gornitzka, A. Martinez, J.-P. Dutasta, Angew. Chem. Int. Ed., 51, 504, (2012)
  • Y. Makita, K. Sugimoto, K. Furuyoshi, K. Ikeda, S. Fujiwara, T. Shin-ike, A. Ogawa, Inorg. Chem., 49, 7220, (2010)
  • Y. Makita, K. Sugimoto, K. Furuyoshi, K. Ikeda, T. Fujita, S. Fujiwara, A. Ogawa, Supramol. Chem., 23, 269, (2011)
  • Y. Makita, K. Furuyoshi, K. Ikeda, T. Fujita, S. Fujiwara, M. Ehara, A. Ogawa, Tetrahedron Lett., 52, 4129, (2011)
  • Y. Makita, K. Ikeda, K. Sugimoto, T. Fujita, T. Danno, K. Bobuatong, M. Ehara, S. Fujiwara, A. Ogawa, J. Organomet. Chem., 706-707, 26, (2012)
  • B. R. James, E. Ochiai, G. L. Rampel, Inorg. Nucl. Chem. Lett., 7, 781, (1971)
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_supcat-2012-0002
Identifiers
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