6533b85cfe1ef96bd12bc0dc
RESEARCH PRODUCT
nBuLi-Mediated hydrophosphination: a simple route to valuable organophosphorus compounds
Claude MoïsePierre Le GendreVirginie ComtePhilippe RichardArnaud Perriersubject
Steric effectsligand designDieneAlkyneConjugated system010402 general chemistryalkynes01 natural sciencesChemical synthesisStyrenechemistry.chemical_compound[ CHIM.ORGA ] Chemical Sciences/Organic chemistryhydrophosphinationOrganic chemistryPhysical and Theoretical ChemistryphosphorusComputingMilieux_MISCELLANEOUSchemistry.chemical_classificationalkenes010405 organic chemistryAlkene[CHIM.ORGA]Chemical Sciences/Organic chemistryOrganic ChemistryRegioselectivity0104 chemical scienceschemistrydescription
A straightforward synthesis of homoallyl- and allylphosphanes has been developed using nBuLi-mediated hydrophosphination of conjugated dienes. In all the cases the phosphorus atom of the reacting phosphane attacked the sterically 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 diffraction studies.
year | journal | country | edition | language |
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2010-03-01 |