6533b82ffe1ef96bd1294ff6

RESEARCH PRODUCT

ChemInform Abstract: nBuLi-Mediated Hydrophosphination: A Simple Route to Valuable Organophosphorus Compounds.

Philippe RichardArnaud PerrierClaude MoïsePierre Le GendreVirginie Comte

subject

Steric effectschemistry.chemical_compoundDienechemistryPhosphorus atomHydrophosphinationGeneral MedicineConjugated systemCombinatorial chemistryStyrene

description

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.

https://doi.org/10.1002/chin.201027171