Pd-Catalyzed Coupling of -Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes.

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling -tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consisted of PdCl(CHCN)/dppp, LiOBu as a base, and cyclopentyl methyl ether as a green solvent. In addition, we performed a gram-scale transformation using NTH derivatives and benzylic phosphates having a C sp-Cl bond. The latter was used as a starting point for further postfunctionalization of the key intermediates.