6304-33-2Relevant academic research and scientific papers
Ni-catalyzed reductive decyanation of nitriles with ethanol as the reductant
Wu, Ke,Ling, Yichen,Sun, Nan,Hu, Baoxiang,Shen, Zhenlu,Jin, Liqun,Hu, Xinquan
supporting information, p. 2273 - 2276 (2021/03/09)
A nickel-catalyzed reductive decyanation of aromatic nitriles has been developed, in which the readily available and abundant ethanol was applied as the hydride donor. Various functional groups on the aromatic rings, such as alkoxyl, amino, imino and amide, were compatible in this catalytic protocol. Heteroaryl, benzylic and alkenyl nitriles were also tolerated. Mechanistic investigation indicated that ethanol provided hydride efficientlyviaβ-hydride elimination in this reductive decyanation.
One-Pot Multi-Component Synthesis of Triarylacrylonitriles Directly by Using CaC2 as a Concise Acetylene Source and K4[Fe(CN)6] as an Eco-Friendly Cyanide Source
Song, Geyang,Li, Zheng
, p. 1326 - 1332 (2018/04/02)
An efficient method for the one-pot multicomponent synthesis of triarylacrylonitriles from various aryl iodides directly by using calcium carbide as a concise acetylene source and potassium hexacyanoferrate(II) as an eco-friendly cyanide source is described. This protocol benefits from safe, inexpensive and easy-to-handle starting materials, good substrate tolerance and simple work-up procedure.
Cyanation of aromatic/vinylic boronic acids with α-cyanoacetates
Wang, Xian-Jin,Zhang, Song-Lin
supporting information, p. 14826 - 14830 (2017/12/15)
A friendly protocol is reported to achieve cyanation of aromatic and vinylic boronic acids using nontoxic and readily available α-cyanoacetates as a cyano source under aerobic conditions. Many aryl/vinyl boronic acids (as well as some iodides and bromides) are amenable substrates to give aryl nitriles and acrylonitriles. This cyanation method provides a safe and operationally convenient alternative to traditional ones requiring toxic cyanide salts.
Exploring highly efficient light conversion agents for agricultural film based on aggregation induced emission effects
Qi, Yunpeng,Wang, Yongtao,Yu, Yongjiang,Liu, Zhiyong,Zhang, Yan,Qi,Zhou, Changtong
, p. 11291 - 11297 (2016/12/09)
Aggregation-induced emission (AIE) is a unique photo-physical phenomenon that has become an emerging and hot research area. It has a wide range of applications due to its excellent luminous properties. In this paper, five compounds and their corresponding light conversion films were prepared based on AIE effects and the thermally activated delayed fluorescence (TADF) phenomenon. Furthermore, ultraviolet conversion, dispersion and photo-physical properties such as UV-vis spectra, fluorescence spectra, and photo stability as well as the mechanical properties of the light conversion films were investigated in detail. The results reveal that triphenylacrylonitrile (TPA) exhibits excellent photo stability and ultraviolet light conversion properties. In addition, the fluorescence emission spectrum of TPA corresponds well with the absorption spectrum of plants in the blue-violet region. In particular, the light conversion film with added TPA also shows enhanced mechanical properties and slightly lower visible light transmittance (3.79%) compared to PVC blank film. Based on the photo stabilities of the five compounds, it can be concluded that the electron-withdrawing cyano group can increase the photo stability of TPA, while carbazole substituents are proved to have an uncertain effect on the rate of photo oxidation, which is attributed to the electron-donating properties of carbazole and increased molecular distortion or rigidity. Finally, it is worth mentioning that this is the first report utilizing AIE-active luminogens (AIEgens) in agricultural light conversion film.
Polymer biquinolyl-containing complexes of Pd(ii) as efficient catalysts for cyanation of aryl and vinyl halides with K4Fe(CN)6
Nikitin, Oleg M.,Polyakova, Olga V.,Sazonov, Petr K.,Yakimansky, Alexander V.,Goikhman, Mikhail Ya.,Podeshvo, Irina V.,Magdesieva, Tatiana V.
, p. 10465 - 10473 (2016/12/07)
A catalytic system for cyanation of aryl and vinyl halides with K4Fe(CN)6 based on a structurally tunable and nontoxic polymer backbone of polyamic type with biquinolyl fragments in the polymer chain capable of coordination to PdII ions is developed. The catalyst is eligible for thermal and microwave activation; in the latter case the reaction time is dramatically decreased. Cyanation of vinyl bromides occurs stereoselectively, and the configuration of the starting alkene is retained; even for Z-isomers the impact of configuration inversion is less than 5%. The polymer-based Pd catalyst is applicable for one-pot multi-step synthesis of the precursors of mesogenic structures of biphenyl type. Consecutive cross-coupling and cyanation reactions can be performed in the presence of the same portion of catalyst, in the same solvent, without isolation of intermediate products.
Rearrangement Reactions of Tritylcarbenes: Surprising Ring Expansion and Computational Investigation
Banert, Klaus,Hagedorn, Manfred,Pester, Tom,Siebert, Nicole,Staude, Cornelius,Tchernook, Ivan,Rathmann, Katharina,Holl?czki, Oldamur,Friedrich, Joachim
, p. 14911 - 14923 (2015/10/19)
As a rule, acetylides and sulfonyl azides do not undergo electrophilic azide transfer because 1,2,3-triazoles are usually formed. We show now that treatment of tritylethyne with butyllithium followed by exposure to 2,4,6-triisopropylbenzenesulfonyl azide leads to products that are easily explained through the generation of short-lived tritylethynyl azide and its secondary product cyanotritylcarbene. Furthermore, it is demonstrated that tritylcarbenes generally do not produce triphenylethenes exclusively, as was stated in the literature. Instead, these carbenes always yielded also (diphenylmethylidene)cycloheptatrienes (heptafulvenes) as side products. This result is supported by static DFT, coupled cluster, and ab initio molecular dynamics calculations. From these investigations, the fused bicyclobutane intermediate was found to be essential for heptafulvene formation. Although the bicyclobutane is also capable of rearranging to the triphenylethene product, only the heptafulvene pathway is reasonable from the energetics. The ethene is formed straight from cyanotritylcarbene.
Synthesis of coumarins via PIDA/I2-mediated oxidative cyclization of substituted phenylacrylic acids
Li, Jinming,Chen, Huiyu,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 4311 - 4320 (2013/04/24)
A variety of functionalized coumarins were synthesized from substituted phenylacrylic acids via PIDA/I2-mediated and irradiation-promoted oxidative carbon-oxygen bond formation. Our studies show that the oxygen in the pendant carboxylic acid group cyclizes favorably to the aryl ring that is cis to it. The main advantages of this method include good functional group tolerance and the transition-metal-free characteristic. The Royal Society of Chemistry 2013.
Palladium-catalyzed three-component arylcyanation of internal alkynes with Aryl bromides and K4[Fe(CN)6]
Cheng, Yi-Nan,Duan, Zheng,Yu, Liujian,Li, Zhongxian,Zhu, Yu,Wu, Yangjie
supporting information; experimental part, p. 901 - 904 (2009/04/07)
The one-pot, palladium-catalyzed, three-component coupling of aryl bromides, internal alkynes, and environmentally friendly K4[Fe(CN) 6] provides an efficient and direct method for the preparation of β-arylalkenylnitriles.
