28269-50-3Relevant articles and documents
Synthesis of Isoindolinones through Intramolecular Amidation of ortho-Vinyl Benzamides
Wei, Wen-tao,Chen, Zhen-yu,Lin, Yong-lu,Chen, Ri-xing,Wang, Qi,Wu, Qing-guang,Liu, Si-jun,Yan, Ming,Zhang, Xue-jing
supporting information, p. 1972 - 1976 (2020/04/20)
A synthetic approach of isoindolinones through intramolecular amidation of ortho-vinyl benzamides was reported. A variety of N-aryl isoindolinone derivatives were prepared in moderate to excellent yields using perfluorobutyl iodide as oxidant. (Figure pre
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.
Stereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles
Hong, Seung Youn,Chang, Sukbok
supporting information, p. 10399 - 10408 (2019/07/08)
Reported herein is a general platform of a stereodefined access to Γ-lactams via Cp*Ir-catalyzed olefin difunctionalization, where in situ generated Ir-nitrenoid is utilized as a key motif of 1,3-dipoles to enable amido transfer in a syn-selective manner.
Steric hindrance effect on the thermo- and photo-responsive properties of pyrene-based polymers
Liao, Junqiu,Liu, Shenglan,Yuan, Yongjie,Zhang, Hailiang
, p. 5698 - 5708 (2018/04/23)
In this work, the influence of the steric hindrance effect between a polymeric backbone and the side groups on the lower critical solution temperature (LCST)-type behavior and photodegradation behavior, respectively, has been carefully studied. A series o
Intramolecular Hydroamidation of ortho-Vinyl Benzamides Promoted by Potassium tert-Butoxide/N,N-Dimethylformamide
Chen, Zhen-Yu,Wu, Liang-Yu,Fang, Hai-Sheng,Zhang, Ting,Mao, Zhi-Feng,Zou, Yong,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 3894 - 3899 (2017/10/07)
An intramolecular hydroamidation of ortho-vinyl benzamides had been developed. The reaction was promoted efficiently by potassium tert-butoxide and N,N-dimethylformamide without the need for strong oxidants or transition-metal catalysts. A series of dihyd
Visible-Light-Mediated Synthesis of Amidyl Radicals: Transition-Metal-Free Hydroamination and N-Arylation Reactions
Davies, Jacob,Svejstrup, Thomas D.,Fernandez Reina, Daniel,Sheikh, Nadeem S.,Leonori, Daniele
supporting information, p. 8092 - 8095 (2016/07/16)
The development of photoredox reactions of aryloxy-amides for the generation of amidyl radicals and their use in hydroamination-cyclization and N-arylation reactions is reported. Owing to the ease of single-electron-transfer reduction of the aryloxy-amides, the organic dye eosin Y was used as the photoredox catalyst, which results in fully transition-metal-free processes. These transformations exhibit a broad scope, are tolerant to several important functionalities, and have been used in the late-stage modification of complex and high-value N-containing molecules.
Rhodium-Catalyzed Hydrocarboxylation of Olefins with Carbon Dioxide
Kawashima, Shingo,Aikawa, Kohsuke,Mikami, Koichi
supporting information, p. 3166 - 3170 (2016/07/19)
The catalytic hydrocarboxylation of styrenes derivatives and α,β-unsaturated carbonyl compounds with CO2(101.3 kPa) in the presence of an air-stable rhodium catalyst was explored. The combination of [RhCl(cod)]2(cod = cyclooctadiene) as a catalyst and diethylzinc as a hydride source allowed for effective hydrocarboxylation and provided the corresponding α-aryl carboxylic acids in moderate to excellent yields. In this catalytic process with carbon dioxide, intervention of the RhI–H species, which could be generated from the RhIcatalyst and diethylzinc, was clarified. Significantly, the catalytic asymmetric hydrocarboxylation of α,β-unsaturated esters with carbon dioxide was also performed by employing a cationic rhodium complex possessing (S)-(–)-4,4′-bi-1,3-benzodioxole-5,5′-diylbis(diphenylphosphine) [(S)-SEGPHOS] as a chiral diphosphine ligand. A plausible model for asymmetric induction was proposed by determination of the absolute configuration of the product.
Asymmetric palladium-catalyzed directed intermolecular fluoroarylation of styrenes
Talbot, Eric P. A.,Fernandes, Talita De A.,McKenna, Jeffrey M.,Toste, F. Dean
supporting information, p. 4101 - 4104 (2014/04/03)
A mild catalytic asymmetric direct fluoro-arylation of styrenes has been developed. The palladium-catalyzed three-component coupling of Selectfluor, a styrene and a boronic acid, provides chiral monofluorinated compounds in good yield and in high enantiom
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.
Catalytic hydroamination of unactivated olefins using a Co catalyst for complex molecule synthesis
Shigehisa, Hiroki,Koseki, Natsumi,Shimizu, Nao,Fujisawa, Mayu,Niitsu, Makoto,Hiroya, Kou
supporting information, p. 13534 - 13537 (2015/02/02)
Functional group tolerance is one of the important requirements for chemical reactions, especially for the synthesis of complex molecules. Herein, we report a mild, general, and functional group tolerant intramolecular hydroamination of unactivated olefins using a Co(salen) complex, an N-fluoropyridinium salt, and a disiloxane reagent. This method, which was carried out at room temperature (or 0 °C), afforded three-, five-, six-, and seven-membered ring nitrogen-containing heterocyclic compounds and was compatible with diverse functional groups.
