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P–C Cross‐Coupling Onto Enamides: Versatile Synthesis of α‐Enamido Phosphane Derivatives
Author(s) -
Cieslikiewicz Monika,
Bouet Alexis,
Jugé Sylvain,
Toffano Martial,
Bayardon Jérôme,
West Caroline,
Lewinski Krzystof,
Gillaizeau Isabelle
Publication year - 2012
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.201101293
Subject(s) - chemistry , boranes , enol , reagent , borane , coupling reaction , combinatorial chemistry , catalysis , medicinal chemistry , stereochemistry , organic chemistry , boron
We report herein the Pd‐catalyzed P–C cross‐coupling reaction between enol phosphates and secondary phosphane–borane complexes or phosphane oxides. The reaction was performed 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 %.