PDF herunterladen
Synthesis 2012(1): 151-157  
DOI: 10.1055/s-0031-1289618
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

5-(p-Tolyl)isoxazol-3-amine-Palladium(II) Complex: Preparation, Structure, and Catalytic Application in the Suzuki-Miyaura Reaction in Water

Vladimir I. Potkin*a, Nikolay A. Bumagin*b, Sergey K. Petkevicha, Alexander S. Lyakhovc, Dmitrii A. Rudakova, Michail V. Livantsovb, Nikita E. Golantsovb
a Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, Surganova Str., 13, Minsk 220072, Belarus
Fax: +375(17)2841679; e-Mail: potkin@ifoch.bas-net.by;
b M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory, 1/3, Moscow 119991, Russian Federation
Fax: +7(495)9328846; e-Mail: bumagin@org.chem.msu.ru;
c Physico-Chemical Research Institute of Belarusian State University, Leningradskaya Str., 14, Minsk 220030, Belarus
Weitere Informationen

Publikationsverlauf

Received 23 September 2011
Publikationsdatum:
23. November 2011 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A air and moisture stable square-planar trans-dichloropalladium(II) complex containing two 5-(p-tolyl)isoxazol-3-amine ligands was synthesized and structurally characterized by single-crystal X-ray diffraction. The isoxazol-3-amine ligand was prepared from 5-(p-tolyl)isoxazole-3-carbaldehyde oxime by successive transformations. The new complex is a high-turnover-number catalyst for the Suzuki-Miyaura reaction with low palladium loading (0.0001-0.1%) in neat water under an air atmosphere.

Key words

5-(p-tolyl)isoxazol-3-amine ligand - palladium complex - crystal structure - catalysis - Suzuki-Miyaura reaction - biaryls - water

    References

  • 1 Miyaura N. Yanagi T. Suzuki A. Synth. Commun.  1981,  11:  513 
    Google Scholar
  • For reviews, see:
  • 2a Miyaura N. Suzuki A. Chem. Rev.  1995,  95:  2457 
    Google Scholar
  • 2b Stanforth SP. Tetrahedron  1998,  54:  263 
    Google Scholar
  • 2c Suzuki A. J. Organomet. Chem.  1999,  576:  147 
    Google Scholar
  • 2d Kotha S. Lahiri K. Kashinath D. Tetrahedron  2002,  58:  9633 
    Google Scholar
  • For selected references, see:
  • 3a Littke AF. Fu GC. Angew. Chem. Int. Ed.  1998,  37:  3387 
    Google Scholar
  • 3b Wolfe JP. Buchwald SL. Angew. Chem. Int. Ed.  1999,  38:  2413 
    Google Scholar
  • 3c Littke AF. Dai C. Fu GC. J. Am. Chem. Soc.  2000,  122:  4020 
    Google Scholar
  • 3d Shaughnessy KH. Booth RS. Org. Lett.  2001,  3:  2757 
    Google Scholar
  • 3e Feuerstein M. Laurenti D. Bougeant C. Doucet H. Santelli M. Chem. Commun.  2001,  325 
    Google Scholar
  • 3f Nishimura M. Ueda M. Miyaura N. Tetrahedron  2002,  58:  5779 
    Google Scholar
  • 3g So CM. Yeung CC. Lau CP. Kwong FY. J. Org. Chem.  2008,  73:  7803 
    Google Scholar
  • 3h Lipshutz BH. Petersen TB. Abela AR. Org. Lett.  2008,  10:  1333 
    Google Scholar
  • 3i Chow WKC. So M. Lau CP. Kwong FY. J. Org. Chem.  2010,  75:  5109 
    Google Scholar
  • 4a Zhang C. Huang J. Trudell ML. Nolan SP. J. Org. Chem.  1999,  64:  3804 
    Google Scholar
  • 4b Tao B. Boykin DW. Tetrahedron Lett.  2002,  43:  4955 
    Google Scholar
  • 4c Najera C. Gil-Molto J. Karlstorm S. Falvello LR. Org. Lett.  2003,  5:  1451 
    Google Scholar
  • 4d Lai Y.-C. Chen H.-Y. Hung W.-C. Lin C.-C. Hong F.-E. Tetrahedron  2005,  61:  9484 
    Google Scholar
  • 4e Xie Y.-X. Li J.-H. Yin D.-L. Chin. J. Org. Chem.  2006,  26:  1155 
    Google Scholar
  • 4f Alacid E. Nájera C. J. Org. Chem.  2009,  74:  2321 
    Google Scholar
  • 4g Nun P. Martinez J. Lamaty F. Synlett  2009,  1761 
    Google Scholar
  • 4h Rahimi A. Schmidt A. Synlett  2010,  1327 
    Google Scholar
  • 4i Lee D.-H. Jin M.-J. Org. Lett.  2011,  13:  252 
    Google Scholar
  • 5a

    Any catalyst with a turnover number (TON) of greater than 10³ is considered as a high-turnover-number catalyst.

  • 5b Darweesh AF. Shaaban MR. Farag AM. Metz P. Dawood KM. Synthesis  2010,  3163 
    Google Scholar
  • For selected earlier references on Suzuki-Miyaura reaction in water, see
  • 6a Bumagin NA. Bykov VV. Beletskaya IP. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.)  1989,  38:  2206 
    Google Scholar
  • 6b Wallow TI. Novak BM. J. Org. Chem.  1994,  59:  5034 
    Google Scholar
  • 6c Campi EM. Jackson WR. Marcuccio SM. Naesland CGM. J. Chem. Soc., Chem. Commun.  1994,  2395 
    Google Scholar
  • 6d Moreno-Manas M. Pajuelo F. Pleixats R. J. Org. Chem.  1995,  60:  6296 
    Google Scholar
  • 6e Bumagin NA. Bykov VV. Tetrahedron  1997,  53:  14437 
    Google Scholar
  • 6f Badone D. Baroni M. Cardamone R. Ielmini A. Guzzi U. J. Org. Chem.  1997,  62:  7170 
    Google Scholar
  • 6g Bumagin NA. Korolev DN. Tetrahedron Lett.  1999,  40:  3057 
    Google Scholar
  • 7a Bumagin NA. Kalinovskii IO. Ponomarev AB. Beletskaya IP. Dokl. Akad. Nauk SSSR  1982,  265:  1138 
    Google Scholar
  • 7b Bumagin NA. Gulevich YV. Beletskaya IP.
    J. Organomet. Chem.  1985,  285:  415 
    Google Scholar
  • 7c Rosschin AI. Kel’chevski SM. Bumagin NA. J. Organomet. Chem.  1998,  560:  163 
    Google Scholar
  • 7d Korolev DN. Bumagin NA. Tetrahedron Lett.  2006,  47:  4225 
    Google Scholar
  • 7e Potkin VI. Petkevich SK. Kurman PV. Russ. J. Org. Chem.  2007,  43:  1622 
    Google Scholar
  • 7f Potkin VI. Petkevich SK. Kurman PV. Russ. J. Org. Chem.  2009,  45:  551 
    Google Scholar
  • 7g Potkin VI. Petkevich SK. Zalesskaya EG. Russ. J. Org. Chem.  2009,  45:  879 
    Google Scholar
  • 8a Petkevich SK. Potkin VI. Kaberdin RV. Russ. J. Org. Chem.  2004,  40:  1146 
    Google Scholar
  • 8b Shakirova OG. Kuratieva NV. Lavrenova LG. Bogomyakov AS. Petkevich SK. Potkin VI. J. Struct. Chem. (Engl. Transl.)  2010,  51:  703 
    Google Scholar
  • 9 Hannah J. Ruyle WV. Jones H. Matzuk KW. Kelly KW. Witzel BE. Holtz WJ. Houser RA. Shen TY. Sarett LH. Lotti VJ. Risley EA. Van Arman CG. Winter CA. J. Med. Chem.  1978,  21:  1093 
    Google Scholar
  • 10 Liu C. Jin L. Lei A. Synlett  2010,  2527 
    Google Scholar
  • 11 Guchhait SK. Kashyap M. Saraf S. Synthesis  2010,  1166 
    Google Scholar
  • 12 Pigge FC. Synthesis  2010,  1745 
    Google Scholar
  • 13 Guo C. Yue X. Qing F.-L. Synthesis  2010,  1837 
    Google Scholar
  • 14 Burla MC. Caliandro R. Camalli M. Carrozzini B. Cascarano GL. De Caro L. Giacovazzo C. Polidori G. Spagna R. J. Appl. Crystallogr.  2005,  38:  381 
    Google Scholar
  • 15 Sheldrick GM. Acta Crystallogr., Sect. A  2008,  64:  112 
    Google Scholar
  • 16 Spek AL. J. Appl. Crystallogr.  2003,  36:  7 
    Google Scholar
  • 18 Leleu A. Fort Y. Schneiderb R. Adv. Synth. Catal.  2006,  348:  1086 
    Google Scholar
  • 19 Copp C. Walls LP. J. Chem. Soc.  1950,  311 
    Google Scholar
  • 20 Wittak DT. Heilman WP. Sankappa SK. J. Med. Chem.  1975,  18:  934 
    Google Scholar
17

CCDC 842425 contains the supplementary crystallographic data for 7. These data can be obtained via http://www.ccdc.cam.ac.uk/conts/retrieving.html, free of charge or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; e-mail: deposit@ccdc.cam.ac.uk or fax: +44(1223)336033.