PDF herunterladen
Synthesis 2005(6): 965-970  
DOI: 10.1055/s-2005-861842
PAPER
© Georg Thieme Verlag Stuttgart · New York

Atom-Economic, Solvent-Free, High Yield Synthesis of 2-(Pyrrol-1-yl)propyldiorganylphosphines

Boris A. Trofimov*a, Nina K. Gusarovaa, Boris G. Sukhova, Svetlana F. Malyshevaa, Olga A. Tarasovaa, Natalya A. Belogorlovaa, Marina A. Maximovaa, Sergey P. Tunikb
a A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia
Fax: +7(3952)419346; e-Mail: mal@irioch.irk.ru;
b Department of Chemistry, St.-Petersburg University, St.-Petersburg, Russia
Weitere Informationen

Publikationsverlauf

Received 20 October 2004
Publikationsdatum:
21. Februar 2005 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

Free-radical addition of secondary phosphines to 1-isopropenylpyrroles (AIBN, 65 °C) proceeds with 100% regioselectivity to give 2-(pyrrol-1-yl)propyldiorganylphosphines in 89-92% isolated yields. This constitutes a highly efficient, atom-economic, solvent-free (‘green’) synthesis of new promising ligands for metal complex catalysts, and potent building blocks for designing of drugs and advanced materials.

Key words

free-radical addition - 1-isopropenylpyrroles - phosphorylation - regioselectivity - P,N-ligands - green chemistry

    References

  • 1a Trofimov BA. Tarasova OA. Mikhaleva AI. Kalinina NA. Sinegovskaya LM. Henkelmann J. Synthesis  2000,  1585 
    Google Scholar
  • 1b Trofimov BA. Tarasova OA. Shemetova MA. Afonin AV. Klyba LV. Baikalova LV. Mikhaleva AI. Zh. Org. Khim.  2003,  39:  437 ; Russ. J. Org. Chem. 2003, 39, 408
    Google Scholar
  • 2 Trofimov BA. Curr. Org. Chem.  2002,  6:  1121 
    CrossrefGoogle Scholar
  • 3 Valentine DH. Hillhouse JH. Synthesis  2003,  2437 
    Artikel in Thieme ConnectGoogle Scholar
  • 4a Trofimov BA. Gusarova NK. Brandsma L. Main Group Chem. News  1996,  4:  18 ; Chem. Abstr. 1996, 125, 142810n
    CrossrefGoogle Scholar
  • 4b Gusarova NK. Malysheva SF. Arbuzova SN. Trofimov BA. Russ. Chem. Bull.  1998,  47:  1645 
    CrossrefGoogle Scholar
  • 4c Trofimov BA. Arbuzova SN. Gusarova NK. Russ. Chem. Rev.  1999,  68:  215 
    CrossrefGoogle Scholar
  • 4d Malysheva SF. Arbuzova SN. In Sovremenniy organicheskiy sintez (Modern Organic Synthesis)   Rakhmankoulov DL. Chemistry; Moscow: 2003.  p.160-177  
    CrossrefGoogle Scholar
  • 5 Nonhebel DC. Walton JC. Free-Radical Chemistry, Structure and Mechanism   University Press; Cambridge: 1974. 
    Google Scholar
  • 6 Trofimov BA. In The Chemistry of Heterocyclic Compounds, Pyrroles   Vol. 48:  Jones RA. Wiley; New York: 1992.  p.131-298  
    Google Scholar
  • 7 Trofimov BA. Malysheva SF. Sukhov BG. Belogorlova NA. Schmidt EYu. Sobenina LN. Kuimov VA. Gusarova NK. Tetrahedron Lett.  2003,  44:  2629 
    CrossrefGoogle Scholar
  • 8a Jacobsen EN. Pfaltz A. Yamamoto H. Comprehensive Asymmetric Catalysis   Springer; Berlin: 1999. 
    CrossrefGoogle Scholar
  • 8b Brunner H. Limmer S. J. Organomet. Chem.  1991,  417:  173 
    CrossrefGoogle Scholar
  • 8c Roucoux A. Suisse I. Devocelle M. Carpentier JF. Agbosson F. Mortreux A. Tetrahedron: Asymmetry  1996,  7:  379 
    CrossrefGoogle Scholar
  • 8d Clarke ML. Cole-Hamilton DJ. Slavin MZ. Woollins JD. Chem. Commun.  2000,  2065 
    CrossrefGoogle Scholar
  • 8e Jang H.-Y. Seo HHJW. Chung YK. Tetrahedron Lett.  2000,  41:  5083 
    CrossrefGoogle Scholar
  • 8f Guo R. Li X. Wu J. Kwok WH. Chen J. Choi MCK. Chan ASC. Tetrahedron Lett.  2002,  43:  6803 
    CrossrefGoogle Scholar
  • 8g Braunstein P. Naud F. Angew. Chem. Int. Ed.  2001,  40:  680 
    CrossrefGoogle Scholar
  • 9 Priola A. Gatti G. Cesca S. Makromol. Chem.  1979,  180:  1 
    CrossrefGoogle Scholar
  • 10 Malysheva SF. Gusarova NK. Belogorlova NA. Nikitin MV. Gendin DV. Trofimov BA. Zh. Obshch. Khim.  1997,  67:  63 ; Russ. J. Gen. Chem. 1997, 67, 58
    Google Scholar
  • 11 Trofimov BA. Gusarova NK. Malysheva SF. Ivanova NI. Sukhov BG. Belogorlova NA. Kuimov VA. Synthesis  2002,  2207 
    Artikel in Thieme ConnectGoogle Scholar
  • 12 Trofimov BA. Gusarova NK. Malysheva SF. Sukhov BG. Belogorlova NA. Kuimov VA. Al’pert ML. Sulfur Lett.  2003,  26:  63 
    CrossrefGoogle Scholar
  • 13 Chelucci G. Orrù G. Pinna GA. Tetrahedron  2003,  59:  9471 
    CrossrefGoogle Scholar
  • 14a Cozzi PG. Zimmermann N. Hilgraf R. Schaffner S. Pfaltz A. Adv. Synth. Catal.  2001,  143:  450 
    Google Scholar
  • 14b Gurevich PA. Yaroshevskaya VA. Chem. Heterocycl. Comp.  2000,  36:  1361 
    Google Scholar
  • 14c Moloy KG. Petersen JL. J. Am. Chem. Soc.  1995,  117:  7707 
    Google Scholar
  • 15 Trofimov BA. Brandsma L. Arbuzova SN. Malysheva SF. Gusarova NK. Tetrahedron Lett.  1994,  35:  7647 
    CrossrefGoogle Scholar
  • 16 Potapov VM. Stereokhimia (Stereochemistry)   Khimia; Moscow: 1988. 
    Google Scholar