A practical synthesis of chiral and achiral phosphonium salts from phosphine borane complexes

Phosphine borane complexes are transformed under mild conditions, in presence of an olefin, into quaternary phosphonium salts by reaction with an alkyl (or aryl) halide. In the case of the reaction of ( R)-PAMP.BH 3 1e with benzyl bromide, the enantiomerically pure phosphonium salt 3h is obtained. P...

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Bibliographic Details
Published in:	Tetrahedron letters Vol. 38; no. 19; pp. 3405 - 3408
Main Authors:	Uziel, Jacques, Riegel, Nadège, Aka, Benoît, Figuière, Pierre, Jugé, Sylvain
Format:	Journal Article
Language:	English
Published:	Elsevier Ltd 12-05-1997
Online Access:	Get full text
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Summary:	Phosphine borane complexes are transformed under mild conditions, in presence of an olefin, into quaternary phosphonium salts by reaction with an alkyl (or aryl) halide. In the case of the reaction of ( R)-PAMP.BH 3 1e with benzyl bromide, the enantiomerically pure phosphonium salt 3h is obtained. Phosphines protected by a borane group can be transformed in “one pot” to quaternary phosphonium salts. The method is applied to the synthesis of various alkyl, aryl, cyclic, fonctionnalized, chiral and achiral phosphonium salts with 50–92%.
ISSN:	0040-4039 1873-3581
DOI:	10.1016/S0040-4039(97)00647-3