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

Boris A. Trofimov; Nina K. Gusarova; Boris G. Sukhov; Svetlana F. Malysheva; Olga A. Tarasova; Natalya A. Belogorlova; Marina A. Maximova; Sergey P. Tunik

doi:10.1055/s-2005-861842

PAPER

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

Boris A. Trofimov*^a, Nina K. Gusarova^a, Boris G. Sukhov^a, Svetlana F. Malysheva^a, Olga A. Tarasova^a, Natalya A. Belogorlova^a, Marina A. Maximova^a, Sergey P. Tunik^b
^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

Abstract

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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

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References

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