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n BuLi‐Mediated Hydrophosphination: A Simple Route to Valuable Organophosphorus Compounds
Author(s) -
Perrier Arnaud,
Comte Virginie,
Moïse Claude,
Richard Philippe,
Le Gendre Pierre
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901407
Subject(s) - chemistry , cycloheptatriene , conjugated system , diene , styrene , organic chemistry , combinatorial chemistry , medicinal chemistry , copolymer , natural rubber , polymer
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.