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Synlett 2008(10): 1581-1582  
DOI: 10.1055/s-2008-1067010
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

Synthetic Applications of Triphenylphosphine

Leandro Ferreira Pedrosa*
Instituto de Química, Universidade Federal Fluminense, UFF, CEP: 24020-150 Niterói, Rio de Janeiro, Brazil
e-Mail: leandropedrosa@globo.com;
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Publication History

Publication Date:
16 May 2008 (online)

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Introduction

Triphenylphosphine (Ph3P) is a very versatile reagent extensively used by organic chemists. Ph3P exists as relatively air-stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether. Ph3P undergoes slow oxidation by air to give triphenylphosphine oxide, Ph3PO. This impurity can be removed by recrystallization of Ph3P from either hot ethanol or hot isopropanol. [1]

Ph3P has received increasing attention as versatile and mild reagent in many occasions for various organic transformations under neutral conditions in recent years. [2]

The properties that guide its usage are its nucleophilicity and its reducing character. [3] The nucleophilicity of Ph3P is indicated by its reactivity toward electrophilic alkenes such as Michael acceptors [4] and alkyl halides. [5]

Ph3P binds well to most transition metals, especially those in the middle and late transition metals of groups 7-10. [6]