1483-36-9Relevant academic research and scientific papers
Rhodium-catalysed addition reaction of aryl- and alkenylboronic acids to isocyanates
Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
, p. 3577 - 3579 (2007)
The addition reaction of aryl- and alkenylboronic acids to isocyanates is catalysed by a rhodium(i) complex, affording secondary amides under mild conditions. The Royal Society of Chemistry.
Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
Chen, Bo,Wu, Xiao-Feng
supporting information, p. 788 - 792 (2020/05/19)
A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
Chen, Bo,Wu, Xiao-Feng
, p. 160 - 163 (2020/02/11)
In this work, an interesting procedure for the synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent has been developed. With palladium as the catalyst and XPhos as the ligand under carbon monoxide pressure, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional group tolerance. Remarkably, this procedure also represents an example on addition of organometallic reagent to isocyanates for α,β-unsaturated amides synthesis.
Synthesis of Amides with Remote Stereocenters by Catalytic Asymmetric γ-Alkynylation of α,β-Unsaturated Amides
Wang, Zi-Xuan,Bai, Xiao-Yan,Yao, Han-Chao,Li, Bi-Jie
supporting information, p. 14872 - 14875 (2016/11/28)
An iridium-catalyzed enantioselective hydroalkynylation of α,β-unsaturated amides was described. The selectivity of this reaction is distinct from that observed in many catalytic hydroalkynylations of α,β-unsaturated carbonyl compounds. It occurs selectively at the γ instead of the β position. Preliminary mechanistic studies suggest that the reaction proceeds through alkene isomerization followed by hydroalkynylation. This method provides a straightforward route for the synthesis of amides with a remote stereocenter at the γ position.
Synthesis of β,γ-unsaturated primary amides from α,β-unsaturated acids and investigation of the mechanism
Theodorou, Vassiliki,Gogou, Marina,Philippidou, Maria,Ragoussis, Valentine,Paraskevopoulos, Georgios,Skobridis, Konstantinos
experimental part, p. 5630 - 5634 (2011/08/22)
α,β-Unsaturated acids, through their acid chlorides, react with tritylamine in the presence of triethylamine under mild conditions, to afford in high yield and high regioselectivity the corresponding β,γ- unsaturated tritylamides. Detritylation with TFA generates quantitatively β,γ-unsaturated primary amides. An investigation of this deconjugative isomerization was performed.
