1311313-26-4Relevant articles and documents
Yb(iii)-catalysedsyn-thioallylation of ynamides
Dutta, Shubham,Gandon, Vincent,Gogoi, Manash Protim,Mallick, Rajendra K.,Prabagar, B.,Sahoo, Akhila K.,Vanjari, Rajeshwer,Yang, Shengwen
supporting information, p. 7521 - 7524 (2021/08/05)
Reported herein is asyn-thioallylation of ynamides incorporating a sulfide moiety at the α-position and an allyl group at the β-position of the ynamide. The transformation is successful under ytterbium(iii)-catalysis, providing access to highly substituted thioamino-skipped-dienes with broad substrate scope. Thus, tetrasubstituted olefins (with four different functional groups: amide, phenyl, thioaryl/alkyl, and allyl on the carbon centers) are made in a single step from readily accessible ynamides, preserving complete atom economy. The reaction can be extended to the synthesis of selenoamino dienes by ynamidesyn-selenoallylation. DFT studies and control experiments provide insight into the reaction mechanism.
Aerobic oxidative alkynylation of H-phosphonates and amides: An efficient route for the synthesis of alkynylphosphonates and ynamides using a recyclable Cu-MnO catalyst
Singh, Harshvardhan,Sahoo, Tapan,Sen, Chiranjit,Galani, Sunil M.,Ghosh, Subhash Chandra
, p. 1691 - 1698 (2019/04/08)
An atom-economical and efficient route for the synthesis of alkynylphosphonates and ynamides by aerobic oxidative alkynylation of H-phosphonates and amides with both aliphatic and aromatic alkynes using our synthesized recyclable heterogeneous Cu-MnO catalyst has been developed. The phosphorylation was carried out under base- and ligand-free conditions, and in the presence of air as the sole oxidant. The reaction is compatible with a wide variety of functional groups and generates alkynylphosphonate and ynamide products in good to excellent yields. Both reactions can be scaled up to the gram scale without any decrease in the reaction yield and the reaction time is less compared to literature reports. The catalyst is recyclable and reused several times without any significant loss of reactivity.
Palladium-Catalyzed Oxygenative Cross-Coupling of Ynamides and Benzyl Bromides by Carbene Migratory Insertion
Gao, Yunpeng,Wu, Guojiao,Zhou, Qi,Wang, Jianbo
supporting information, p. 2716 - 2720 (2018/02/13)
A palladium-catalyzed oxygenative cross-coupling of ynamides and benzyl bromides has been developed. After subsequent hydrogenation, α,α-disubstituted amide derivatives were obtained in good yields. Migratory insertion of α-oxo palladium carbene species, generated by intermolecular oxidation, is proposed as the key step in this reaction. The study demonstrates the potential of ynamides to serve as carbene precursors in palladium-catalyzed C?C bond-forming cross-coupling reactions.
