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Synthesis 2010(11): 1924-1928  
DOI: 10.1055/s-0029-1218705
PSP
© Georg Thieme Verlag Stuttgart ˙ New York

Economic Large-Scale Synthesis of o- and m-Diphenylphosphinobenzoic Acids

Susanne T. Kemme, Yvonne Schmidt, Christian U. Grünanger, Andy C. Laungani, Christian Herber, Bernhard Breit*
Albert-Ludwigs-Universität Freiburg, Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albertstr. 21, 79104 Freiburg im Breisgau, Germany
Fax: +49(761)2038715; e-Mail: Bernhard.Breit@chemie.uni-freiburg.de;
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Publication History

Received 17 February 2010
Publication Date:
15 March 2010 (online)

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Abstract

An efficient and simple to perform large-scale synthesis of o- and m-diphenylphosphinobenzoic acids is presented. In a single step, both useful carboxylic acid-functionalized phosphines can be accessed starting from the same inexpensive bulk chemicals o-chlorobenzoic acid, triphenylphosphine, and sodium. In both cases the formation of the desired product is controlled by the ratio of the starting materials only. Additionally, X-ray crystallographic data are reported for both products.

Key words

phosphorus ligand - catalysis - aromatic carboxylic acid - directing group - Birch conditions

    References

  • 1 Phosphorus Ligands in Asymmetric Catalysis, Synthesis and Applications   Börner A. Wiley-VCH; Weinheim: 2008. 
  • 2a Trost BM. Van Vranken DL. Angew. Chem. Int. Ed.  1992,  31:  228 
    Search in Google Scholar
  • 2b Trost BM. Li L. Guile SD. J. Am. Chem. Soc.  1992,  114:  8747 
    Search in Google Scholar
  • 2c Trost BM. Van Vranken DL. Bingel C. J. Am. Chem. Soc.  1992,  114:  9327 
    Search in Google Scholar
  • 2d Kim YK. Lee SJ. Ahn KH. J. Org. Chem.  2000,  65:  7807 
    Search in Google Scholar
  • 2e Song CE. Yang JW. Roh EJ. Lee S.-G. Ahn JH. Han H. Angew. Chem. Int. Ed.  2002,  41:  9852 
    Search in Google Scholar
  • 2f Trost BM. Breit B. Organ MG. Tetrahedron Lett.  1994,  35:  5817 
    Search in Google Scholar
  • 2g Breit B. Chem. Commun.  1996,  2071 
  • 3a Saxon E. Bertozzi CR. Science  2000,  287:  2007 
    Search in Google Scholar
  • 3b Kiick KL. Saxon E. Tirrell DA. Bertozzi CR. Proc. Natl. Acad. Sci. U.S.A.  2002,  99:  19 
    Search in Google Scholar
  • 4a Mino T. Kashihara K. Yamashita M. Tetrahedron: Asymmetry  2001,  12:  287 
    Search in Google Scholar
  • 4b Schenkel LB. Ellman JA. Org. Lett.  2003,  5:  545 
    Search in Google Scholar
  • 4c Marinho VR. Rodrigues AI. Burke AJ. Tetrahedron: Asymmetry  2008,  19:  454 
    Search in Google Scholar
  • 4d Parisot S. Kolodziuk R. Goux-Henry C. Iourtchenkoa A. Sinoua D. Tetrahedron Lett.  2002,  43:  7397 
    Search in Google Scholar
  • 4e Ongeri S. Piarulli U. Roux M. Montia C. Gennari C. Helv. Chim. Acta  2002,  85:  3388 
    Search in Google Scholar
  • 4f Hird AW. Hoveyda AH. Angew. Chem. Int. Ed.  2003,  42:  1276 
    Search in Google Scholar
  • 4g Breit B. Laungani A. Tetrahedron: Asymmetry  2003,  14:  3823 
    Search in Google Scholar
  • 4h Thomas CM. Mafua R. Therrien B. Rusanov E. Stoeckli-Evans H. Süss-Fink G. Chem. Eur. J.  2002,  8:  3343 
    Search in Google Scholar
  • For copper-mediated reactions, see:
  • 5a Breit B. Schmidt Y. Chem. Rev.  2008,  108:  2928 
    Search in Google Scholar
  • For additions, see:
  • 5b Breit B. Angew. Chem. Int. Ed.  1998,  37:  525 
    Search in Google Scholar
  • 5c Breit B. Zahn SK. Tetrahedron Lett.  1998,  39:  1901 
    Search in Google Scholar
  • 5d Breit B. Zahn SK. Polyhedron  2000,  19:  513 
    Search in Google Scholar
  • 6a Breit B. Demel P. Adv. Synth. Catal.  2001,  343:  429 
    Search in Google Scholar
  • 6b Demel P. Keller M. Breit B. Chem. Eur. J.  2006,  12:  6669 
    Search in Google Scholar
  • 6c Breit B. Demel P. Grauer D. Studte C. Chem. Asian J.  2006,  1:  586 
    Search in Google Scholar
  • 6d Breit B. Grünanger CU. Abillard O. Eur. J. Org. Chem.  2007,  2497 
  • 7a Breit B. Liebigs Ann. Chem.  l997,  1841 
  • 7b Breit B. Dauber M. Harms K. Chem. Eur. J.  1999,  5:  2819 
    Search in Google Scholar
  • 7c Breit B. Demel P. Gebert A. Chem. Commun.  2004,  114 
  • 7d Burke SD. Cobb JE. Tetrahedron Lett.  1986,  4237 
  • 8a Herber C. Breit B. Chem. Eur. J.  2006,  12:  6684 
    Search in Google Scholar
  • 8b Herber C. Breit B. Eur. J. Org. Chem.  2007,  3512 
  • 8c Rein C. Demel P. Outten RA. Netscher T. Breit B. Angew. Chem. Int. Ed.  2007,  46:  8670 
    Search in Google Scholar
  • 8d Reiss T. Breit B. Org. Lett.  2009,  11:  3286 
    Search in Google Scholar
  • 8e Schmidt Y. Breit B. Org. Lett.  2009,  11:  4767 
    Search in Google Scholar
  • 9a Amengual R. Genin E. Michelet V. Savignac M. Genêt P. Adv. Synth. Catal.  2002,  344:  393 
    Search in Google Scholar
  • 9b Kozlov VA. Aleksanyan DV. Nelyubina YV. Lyssenko KA. Gutsul EI. Puntus LN. Vasil’ev AA. Petrovskii PV. Odinets IL. Organometallics  2008,  7:  4062 
    Search in Google Scholar
  • 9c Genin E. Amengual R. Michelet V. Savignac M. Jutand A. Neuville L. Genêt J.-P. Adv. Synth. Catal.  2004,  346:  1733 
    Search in Google Scholar
  • 9d Kawatsura M. Ikeda D. Komatsu Y. Mitani K. Tanaka T. Uenishi J. Tetrahedron  2007,  63:  8815 
    Search in Google Scholar
  • 10a Laungani AC. Slattery M. Krossing I. Breit B. Chem. Eur. J.  2008,  14:  4488 
    Search in Google Scholar
  • 10b Laungani A. Breit B. Chem. Commun.  2008,  844 
  • o-DPPBA:
  • 11a Refosco F. Tiato F. Bandoli G. Deutsch E. J. Chem Soc., Dalton Trans.  1993,  2901 
  • 11b Ravindar V. Helming H. Schumann H. Blum J. Synth. Commun.  1992,  22:  1453 
    Search in Google Scholar
  • m-DPPBA:
  • 11c Schiemenz GP. Siebeneick H.-U. Chem. Ber.  1969,  102:  1883 
    Search in Google Scholar
  • 11d Ravindar V. Hemling H. Schumann H. Blum J. Synth. Commun.  1992,  22:  841 
    Search in Google Scholar
  • o-DPPBA and m-DPPBA:
  • 12a Herd O. Heßler A. Hingst M. Tepper M. Stelzer O. J. Organomet. Chem.  1996,  522:  69 
    Search in Google Scholar
  • 12b Veits YA. Neganova EG. Vinogradova OS. Russ. J. Gen. Chem.  2005,  1060 
  • o-DPPBA:
  • 12c Kim YK. Lee SJ. Ahn KH. J. Org. Chem.  2000,  65:  7807 
    Search in Google Scholar
  • 12d Stadler A. Kappe CO. Org. Lett.  2002,  4:  3541 
    Search in Google Scholar
  • m-DPPBA:
  • 12e Tsevtkov EN. Lobanov DI. Makhamatkhanov MM. Kabachnik MI. Tetrahedron  1969,  25:  5623 
    Search in Google Scholar
  • 12f Tsvetkov EN. Lobanov DI. Kabachnik MI. Teoret. Eksper. Khim.  1966,  2:  458 ; Chem. Abstr. 1967, 66, 28299r
    Search in Google Scholar
  • o-DPPBA and m-DPPBA:
  • 13a Hingst M. Tepper M. Stelzer O. Eur. J. Inorg. Chem.  1998,  73 
  • o-DPPBA:
  • 13b Issleib K. Zimmermann H. Z. Anorg. Allg. Chem.  1967,  353:  197 
    Search in Google Scholar
  • m-DPPBA:
  • 13c Gilman H. Brown GE. J. Am. Chem. Soc.  1945,  67:  824 
    Search in Google Scholar
  • 13d Schindlbauer H. Monatsh. Chem.  1965,  96:  1021 
    Search in Google Scholar
  • 14 Hoots JE. Rauchfuss TB. Wrobleski DA. Inorg. Synth.  1982,  21:  175 
    Search in Google Scholar
  • 15 Laungani AC. Keller M. Slattery JM. Krossing I. Breit B. Chem. Eur. J.  2009,  15:  10405 
    CrossrefSearch in Google Scholar