n BuLi‐Mediated Hydrophosphination: A Simple Route to Valuable Organophosphorus Compounds

A straightforward synthesis of homoallyl‐ and allylphosphanes has been developed using n BuLi‐mediated hydrophosphination of conjugated dienes. In all the cases the phosphorus atom of the reacting phosphane attacked thesterically less demanding side of the diene exclusively. In addition, high regios...

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Veröffentlicht in:European journal of organic chemistry 2010-03, Vol.2010 (8), p.1562-1568
Hauptverfasser: Perrier, Arnaud, Comte, Virginie, Moïse, Claude, Richard, Philippe, Le Gendre, Pierre
Format: Artikel
Sprache:eng
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Zusammenfassung:A straightforward synthesis of homoallyl‐ and allylphosphanes has been developed using n BuLi‐mediated hydrophosphination of conjugated dienes. In all the cases the phosphorus atom of the reacting phosphane attacked thesterically less demanding side of the diene exclusively. In addition, high regioselectivities towards 1,2‐ or 1,4‐addition products were observed depending on the nature of the dienes. This hydrophosphination reaction was extended to a variety of substrates such as styrene derivatives, alkynes and 1,3,5‐cycloheptatriene. The structures of three hydrophosphination products were confirmed by X‐ray diffractionstudies.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200901407