78871-05-3Relevant academic research and scientific papers
B(C6F5)3-catalyzed O-H insertion reactions of diazoalkanes with phosphinic acids
Jiang, Jun,Zhang, Xinzhi,Zhang, Yangyang,Zhao, Jincheng
supporting information, p. 5772 - 5776 (2021/07/12)
A highly efficient base-, metal-, and oxidant-free catalytic O-H insertion reaction of diazoalkanes and phosphinic acids in the presence of B(C6F5)3has been developed. This powerful methodology provides a green approach towards the synthesis of a broad spectrum of α-phosphoryloxy carbonyl compounds with good to excellent yields (up to 99% yield). The protocol features the advantages of operational simplicity, high atom economy, practicality, easy scalability and environmental friendliness.
Organic photoredox catalytic α-C(sp3)-H phosphorylation of saturated: Aza -heterocycles
Yi, Ming-Jun,Xiao, Teng-Fei,Li, Wen-Hui,Zhang, Yi-Fan,Yan, Pen-Ji,Zhang, Baoxin,Xu, Peng-Fei,Xu, Guo-Qiang
supporting information, p. 13158 - 13161 (2021/12/16)
A metal-free C(sp3)-H phosphorylation of saturated aza-heterocycles via the merger of organic photoredox and Br?nsted acid catalyses was established under mild conditions. This protocol provided straightforward and economic access to a variety of valuable α-phosphoryl cyclic amines by using commercially available diarylphosphine oxide reagents. In addition, the D-A fluorescent molecule DCQ was used for the first time as a photocatalyst and exhibited an excellent photoredox catalytic efficiency in this transformation. A series of mechanistic experiments and DFT calculations demonstrated that this transformation underwent a sequential visible light photoredox catalytic oxidation/nucleophilic addition process.
Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution
Lei, Tao,Liang, Ge,Cheng, Yuan-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 5385 - 5389 (2020/07/08)
Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.
Nitrogen-phosphorus ligand, and preparation method and application thereof
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Paragraph 0162-0165, (2020/01/03)
The invention belongs to the field of organic chemical ligands, and discloses a nitrogen-phosphorus ligand which has a structure shown in a general formula I, wherein R is hydrogen or alkoxy, R iscyclohexyl, naphthyl and optionally substituted phenyl, and R is hydrogen, phenyl or alkyl. The invention also discloses four synthesis methods of the nitrogen-phosphorus ligand and an applicationof the nitrogen-phosphorus ligand in a Sonogashira asymmetric cross-coupling reaction. According to the invention, the nitrogen-phosphorus compound with a novel structure is synthesized through derivatization by taking quinine and cinchonine as core frameworks, and the nitrogen-phosphorus compound can be used as a ligand for the asymmetric reaction. Particularly, the electronic effect and steric hindrance effect of phosphorus on the ligand can be regulated and controlled, so that the nitrogen-phosphorus compound has the following unique advantages in the free radical asymmetric reaction: catalytic efficiency is high, the application range of substrates is wide, the yield is high, and enantioselectivity is good.
Asymmetric Hydroformylation of Vinyl Acetate with DIOP-Type Ligands
Hobbs, Charles F.,Knowles, W. S.
, p. 4422 - 4427 (2007/10/02)
The rhodium-catalyzed hydroformylation of vinyl acetate and related esters was carried out in the presence of chiral phosphine ligands of the DIOP type to give the corresponding optically active 2-(acyloxy)propanal, a precursor for the amino acid threonine.Ligand structure and the ligand/metal ratio were the primary factors controlling asymmetric induction; temperature, CO pressure, and solvent polarity had minor effects.The highest induction efficiencies, up to 51 percent ee, were obtained with the 5H-dibenzophospholyl derivative of DIOP (DIPHOL, 1e).
