74471-18-4Relevant academic research and scientific papers
Dual aminoquinolate diarylboron and nickel catalysed metallaphotoredox platform for carbon-oxygen bond construction
Day, Craig,Jia, Xin,Wei, Lanfeng,Xu, Liang,Zu, Weisai
supporting information, p. 8273 - 8276 (2020/08/17)
Herein, aminoquinolate diarylboron complexes are utilized as photocatalysts in dual Ni/photoredox catalyzed carbon-oxygen construction reactions. Via this unified metallaphotoredox platform, diverse (hetero)aryl halides can be conveniently coupled with acids, alcohols and water. This method features operational simplicity, broad substrate scope and good compatibility with functional groups. This journal is
Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction
Chen, Zhengwang,Wen, Xiaowei,Zheng, Weiping,He, Ruolan,Chen, Dou,Cao, Dingsheng,Long, Lipeng,Ye, Min
, p. 5691 - 5701 (2020/04/10)
Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.
Equilibrium shift in the rhodium-catalyzed acyl transfer reactions
Arisawa, Mieko,Igarashi, Yui,Kobayashi, Haruki,Yamada, Toru,Bando, Kentaro,Ichikawa, Takuya,Yamaguchi, Masahiko
, p. 7846 - 7859 (2011/10/12)
Rhodium/phosphine complexes catalyze equilibrium acyl transfer reactions between acid fluorides, aryl esters, acylphosphine sulfides, and thioesters. The use of appropriate co-substrates to accept heteroatom groups shifted the equilibrium to desired products. Acylphosphine sulfides and aryl esters were converted to acid fluorides using benzoylpentafluorobenzene as the fluoride donor, and the fluorination reaction of thioesters employed (4-tolylthio) pentafluorobenzene. Acid fluorides were converted into acylphosphine sulfides and thioesters using diphosphine disulfides and disulfides/triphenylphosphine, respectively. Aryl esters were obtained from acid fluorides and phenols in the presence of triphenylsilane. Aryl esters, acylphosphine sulfides, and thioesters were also interconverted in the presence of rhodium complexes. These rhodium-catalyzed acyl transfer reactions proceeded under neutral conditions without using acid or base. The involvement of acyl rhodium intermediates in these reactions was suggested by the carbothiolation reaction of thioesters and alkynes.
Evidence of substituent-induced electronic interplay. Effect of the remote aromatic ring substituent of phenyl benzoates on the sensitivity of the carbonyl unit to electronic effects of phenyl or benzoyl ring substituents
Neuvonen, Helmi,Neuvonen, Kari,Pasanen, Paavo
, p. 3794 - 3800 (2007/10/03)
Carbonyl carbon 13C NMR chemical shifts δC(C=O) measured in this work for a wide set of substituted phenyl benzoates p-Y-C 6H4CO2C6H4-p-X (X = NO2, CN, Cl, Br, H, Me, or MeO; Y = NO2, Cl, H, Me, MeO, or NMe2) have been used as a tool to study substituent effects on the carbonyl unit. The goal of the work was to study the cross-interaction between X and Y in that respect. Both the phenyl substituents X and the benzoyl substituents Y have a reverse effect on δC(C=O). Electron-withdrawing substituents cause shielding while electron-donating ones have an opposite influence, with both inductive and resonance effects being significant. The presence of cross-interaction between X and Y could be clearly verified. Electronic effects of the remote aromatic ring substituents systematically modify the sensitivity of the C=O group to the electronic effects of the phenyl or benzoyl ring substituents. Electron-withdrawing substituents in one ring decrease the sensitivity of δC(C=O) to the substitution of another ring, while electron-donating substituents inversely affect the sensitivity. It is suggested that the results can be explained by substituent-sensitive balance of the contributions of different resonance structures (electron delocalization, Scheme 1).
Conversion of N-aromatic amides to O-aromatic esters
Glatzhofer, Daniel T.,Roy, Raymond R.,Cossey, Kimberly N.
, p. 2349 - 2352 (2007/10/03)
(Matrix Presented) N-Aromatic secondary amides can be transformed into O-aromatic esters in high yield via N-nitrosamide intermediates. The amides can be generated in situ from the corresponding aromatic amines or nitro compounds, and phenols can easily be made from the esters. The reaction can be modified by addition of methyl methacrylate or toluene at 0 °C to give polymerization or deamination, respectively. The rearrangement mechanism may involve radical formation and recombination.
