114475-19-3Relevant articles and documents
Palladium-Catalyzed Aminocarbonylation of Allylic Alcohols
Li, Haoquan,Neumann, Helfried,Beller, Matthias
supporting information, p. 10050 - 10056 (2016/07/19)
A benign and efficient palladium-catalyzed aminocarbonylation reaction of allylic alcohols is presented. The generality of this novel process is demonstrated by the synthesis of β,γ-unsaturated amides including aliphatic, cinnamyl, and terpene derivatives. The choice of ligand is crucial for optimal carbonylation processes: Whereas in most cases the combination of PdCl2with Xantphos (L6) gave best results, sterically hindered substrates performed better in the presence of simple triphenylphosphine (L10), and primary anilines gave the best results using cataCXium PCy (L8). The reactivity of the respective catalyst system is significantly enhanced by addition of small amounts of water. Mechanistic studies and control experiments revealed a tandem allylic alcohol amination/C?N bond carbonylation reaction sequence.
One-pot amide synthesis from allyl or benzyl halides and amines by Pd-catalysed carbonylation
Troisi, Luigino,Granito, Catia,Rosato, Francesca,Videtta, Valeria
experimental part, p. 371 - 373 (2010/03/24)
Amides can be prepared from allyl or benzyl halides and primary or secondary amines, using Pd(0) catalyst under CO pressure, in a one-pot synthesis. The reaction proceeds through the acyl palladium halide formation which undergoes an acylic nucleophilic substitution from the amine.
Synthesis of γ-hydroxy α,β-unsaturated amides by base induced isomerization of epoxy amides
Brooks, Peter B.,Marson, Charles M.
, p. 9613 - 9622 (2007/10/03)
Treatment of 3,4-epoxyamides with LDA affords γ-hydroxy-α,β- unsaturated amides, usually with high (E)-selectivity. The 3,4-epoxyamides were prepared by the epoxidation of β,γ-unsaturated amides with meta- chloroperbenzoic acid.
