65680-40-2Relevant academic research and scientific papers
Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
supporting information, p. 1468 - 1488 (2019/01/25)
Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Preparation of isoindolinones via a palladium-catalyzed diamination
Li, Yu,Kou, Xuezhen,Ye, Chenghao,Zhang, Xinghua,Yang, Guoqiang,Zhang, Wanbin
supporting information, p. 285 - 288 (2017/01/03)
A Pd(II)-catalyzed cyclization using oxidative olefin diamination was developed for the preparation of isoindolinones from ortho-olefinic N-methoxybenzamides. Using the optimized reaction conditions, the desired products were obtained in up to 90% yield using NFSI as the oxidant. This reaction provides an efficient and direct access to isoindolinones with amine functionality, an important drug skeleton.
Enantioselective Palladium(II)-Catalyzed Intramolecular Aminoarylation of Alkenes by Dual N?H and Aryl C?H Bond Cleavage
Zhang, Wen,Chen, Pinhong,Liu, Guosheng
supporting information, p. 5336 - 5340 (2017/04/27)
An asymmetric palladium-catalyzed intramolecular oxidative aminoarylation of alkenes has been developed with quinoline–oxazoline chiral ligands and Ag2CO3 as the oxidant. Various indolines containing a quaternary stereogenic center were synthesized in high yield with excellent enantioselectivity. Preliminary mechanistic studies suggest that the addition of a catalytic amount of phenylglyoxylic acid significantly accelerates the reaction and slightly enhances the enantioselectivity.
Palladium-Catalyzed Intramolecular Insertion of Alkenes into the Carbon-Nitrogen Bond of β-Lactams
Yada, Akira,Okajima, Satoshi,Murakami, Masahiro
supporting information, p. 8708 - 8711 (2015/07/27)
The carbon-nitrogen bond of β-lactams is cleaved by palladium(0), and an alkene is intramolecularly inserted therein. The following reductive elimination produces nitrogen-containing benzo-fused tricycles in good to high yields.
Palladium-Catalyzed Aerobic Aminooxygenation of Alkenes for Preparation of Isoindolinones
Kou, Xuezhen,Li, Yu,Wu, Liang,Zhang, Xinghua,Yang, Guoqiang,Zhang, Wanbin
, p. 5566 - 5569 (2015/12/01)
A palladium-catalyzed intramolecular isoindolinone-forming aminooxygenation of alkenes with 1 atm of oxygen as oxidant is reported. A variety of functionalized alkenes and carboxylic acids can be used, and high yields were observed. Preliminary mechanistic studies revealed that the aminooxygenation products were formed through the oxidation of a C-PdII species using a strong oxidant, peroxide, which is generated in situ from a Pd(OAc)2/bpy/O2/HOAc catalytic system.
Copper-mediated/catalyzed oxyalkylation of alkenes with alkylnitriles
Bunescu, Ala,Wang, Qian,Zhu, Jieping
supporting information, p. 14633 - 14636 (2015/01/09)
A copper-promoted oxyalkylation of alkenes with alkylnitriles has been developed. The protocol provides rapid access to phthalides (γ-lactones) or isochromanones (d-lactones) via the formation of a C(sp3)-C(sp3) and a C(sp3)-O bond with the generation of up to two quaternary carbon atoms. Mechanistic studies suggest that this reaction is initiated by the formation of the C(sp3)-C(sp3) bond rather than the C(sp3)-O bond. Catalytic conditions were subsequently developed using carboxylic acid as an internal nucleophile.
Pd-Catalyzed intramolecular oxyalkynylation of alkenes with hypervalent iodine
Nicolal, Stefano,Erard, Stephane,Gonzalez, Davinla Fernandez,Waser, Jerome
supporting information; experimental part, p. 384 - 387 (2010/03/04)
(Figure presented) The first example of intramolecular oxyalkynylation of nonactivated alkenes using oxidative Pd chemistry is reported. Both phenol and aromatic or aliphatic acid derivatives could be used under operator-friendly conditions (room temperature, technical solvents, under air). The discovery of the superiority of benzlodoxolone-derlved hypervalent iodine reagent 3d as an alkyne transfer reagent further expands the rapidly increasing utility of hypervalent iodine reagents in catalysis and is expected to have important implications for other similar processes.
