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

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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