6533b82ffe1ef96bd1295bc4

RESEARCH PRODUCT

P-C Cross-Coupling Onto Enamides: Versatile Synthesis of α-Enamido Phosphane Derivatives

Alexis BouetIsabelle GillaizeauMartial ToffanoKrzystof LewinskiCaroline WestMonika CieslikiewiczMonika CieslikiewiczSylvain JugéJérôme Bayardon

subject

phosphaalkenesStereochemistryboranesOrganic ChemistryphosphanesBoranesPhosphateEnolMedicinal chemistryCoupling (electronics)chemistry.chemical_compoundchemistryenolsReagentcross-couplingPhysical and Theoretical Chemistry

description

We report herein the Pd-catalyzed P–C cross-coupling reac- tion between enol phosphates and secondary phosphane–bor- ane complexes or phosphane oxides. The reaction was per- formed under mild conditions, owing to Pd activation of the P–H bonds of the phosphane–boranes (or phosphane oxides) and to the powerful enol phosphate coupling reagents. New useful chiral and achiral α - β -alkenylphosphane derivatives bearing an amido group in the α -position to the P center were obtained in yields up to 70 %.

https://doi.org/10.1002/ejoc.201101293