934-85-0Relevant articles and documents
Nickel-Catalyzed Directed C6-Selective C-H Alkylation of 2-Pyridones with Dienes and Activated Alkenes
Miura, Wataru,Hirano, Koji,Miura, Masahiro
, p. 5337 - 5344 (2017)
A pyridine-directed, C6-selective nickel-catalyzed ring-contracting C-H alkylation of 2-pyridones with 1,5-cyclooctadiene (cod) has been developed. The reaction proceeds smoothly under external-ligand-free conditions and is accelerated uniquely by a K3PO4 base. Preliminary mechanistic investigations with deuterium-labeled substrates and related reactions with some alkenes are also disclosed.
Asymmetric Markovnikov Hydroaminocarbonylation of Alkenes Enabled by Palladium-Monodentate Phosphoramidite Catalysis
Yao, Ya-Hong,Yang, Hui-Yi,Chen, Ming,Wu, Fei,Xu, Xing-Xing,Guan, Zheng-Hui
supporting information, p. 85 - 91 (2021/01/12)
A palladium-catalyzed asymmetric Markovnikov hydroaminocarbonylation of alkenes with anilines has been developed for the atom-economical synthesis of 2-substituted propanamides bearing an α-stereocenter. A novel phosphoramidite ligand L16 was discovered which exhibited very high reactivity and selectivity in the reaction. This asymmetric Markovnikov hydroaminocarbonylation employs readily available starting materials and tolerates a wide range of functional groups, thus providing a facile and straightforward method for the regio- and enantioselective synthesis of 2-substituted propanamides under ambient conditions. Mechanistic studies revealed that the reaction proceeds through a palladium hydride pathway.
Phosphonium Phenolate Zwitterion vs Phosphonium Ylide: Synthesis, Characterization and Reactivity Study of a Trimethylphosphonium Phenolate Zwitterion
Xiao, Jing,Li, Qiang,Shen, Ruwei,Shimada, Shigeru,Han, Li-Biao
supporting information, p. 5715 - 5720 (2019/11/22)
4-Methoxy-3-(trimethylphosphonio)phenolate was obtained from a regioselective addition of PMe3 to p-quinone monoacetal. This compound undergoes hydrogen isotope exchange with D2O or CD3CN, and is capable of catalyzing H/D exchange of CD3CN with substrates bearing weakly acidic hydrogens. It exhibits similar reactivity to phosphorus ylides for olefinations of aldehydes. A possible tautomerization between the phosphonium phenolate zwitterion and phosphonium ylide is proposed for the first time to rationalize the unique reactivity.