10137-80-1Relevant articles and documents
Synthesis, structures of benzoxazolyl iridium(III) complexes, and applications on C-C and C-N bond formation reactions under solvent-free conditions: Catalytic activity enhanced by noncoordinating anion without silver effect
Wang, Dawei,Zhao, Keyan,Xu, Chongying,Miao, Hongyan,Ding, Yuqiang
, p. 3910 - 3918 (2014)
Several new bisbenzoxazolyl iridium(III) complexes have been synthesized and characterized through X-ray crystallography. These complexes exhibit excellent catalytic activity in C-C and C-N bond formation reactions from the alkylation of amine with amine, amine with alcohol, ketone with alcohol, and alcohol with alcohol through a borrowing hydrogen reaction. Moreover, these iridium(III) complexes are effective catalysts for the alkylation of amine with alcohol and ketone with alcohol under solvent-free conditions. The catalytic activity of these complexes is greatly enhanced by noncoordinating, while the experiments have excluded the possibility of a "silver effect" (bimetallic catalysis or silver-assisted metal catalysis) from the experiments.
Silver/manganese dioxide nanorod catalyzed hydrogen-borrowing reactions and tert-butyl ester synthesis
Luo, Huanhuan,Wang, Dawei,Xu, Zhaojun,Yang, Bobin,Yang, Yike
, p. 708 - 715 (2021)
Silver/manganese dioxide (Ag@MnO2) nanorods are synthesized and characterized by scanning electron microscopy, transmission electron microscopy, energy dispersive X-ray spectroscopy, X-ray powder diffraction, and X-ray photoelectron spectroscopy. It was discovered that Ag@MnO2 nanorods can realize hydrogen-borrowing reactions in high yields and are also effective for the synthesis of tert-butyl esters from aryl cyanides and tert-butyl hydroperoxide in a short period of time. Mechanistic experiments revealed that this catalytic system acts as a Lewis acid in hydrogen-borrowing reactions, while the synthesis of tert-butyl esters occurs through a radical pathway. This is the first report on the excellent catalytic activity of Ag@MnO2 nanorods as a catalyst.
Continuous flow heterogeneous catalytic reductive aminations under aqueous micellar conditions enabled by an oscillatory plug flow reactor
?tv?s, Sándor B.,Buchholcz, Balázs,Darvas, Ferenc,Kappe, C. Oliver,Novák, Zoltán,Sipos, Gellért,Wernik, Michaela
, p. 5625 - 5632 (2021)
Despite the fact that continuous flow processing exhibits well-established technical advances, aqueous micellar chemistry, a field that has proven extremely useful in shifting organic synthesis to sustainable water-based media, has mostly been explored under conventional batch-based conditions. This is particularly because of the fact that the reliable handling of slurries and suspensions in flow has been considered as a significant technical challenge. Herein, we demonstrate that the strategic application of an oscillatory plug flow reactor enables heterogeneous catalytic reductive aminations in aqueous micellar media enhancing mass transport and facilitating process simplicity, stability and scalability. The micellar flow process enabled a broad range of substrates, including amino acid derivatives, to be successfully transformed under reasonably mild conditions utilizing only very low amounts of Pd/C as a readily available heterogeneous catalyst. The preparative capabilities of the process along with the recyclability of the heterogenous catalyst and the aqueous reaction media were also demonstrated. This journal is
Elucidating the impact of N-arylanilino substituents of squaraines on their photovoltaic performances
Yang, Daobin,Hayashi, Yuya,Sasabe, Hisahiro,Igarashi, Tsukasa,Sano, Takeshi,Kido, Junji
, p. 188 - 194 (2019)
Squaraines have attracted increasing research attention for organic photovoltaic applications because of their facile and low-cost synthesis, and intense and broad absorption in the visible and near-infrared (Vis-NIR) regions. Herein, three new squaraines, N-phenylanilino substituted SQ-EP, N-2-naphthylanilino substituted SQ-EN, and N-fluorenylanilino substituted SQ-EF, were developed for improving the hole mobility of aniline-based squaraines. The substitution effect of N-arylanilino groups on the optoelectronic properties of squaraines was investigated. These squaraines exhibited similar absorbance spectra, HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels, and hole mobilities in their neat films. However, compared to their neat films, the hole mobility of the SQ-EP-based BHJ blend film showed the smallest decrease when blending with PC71BM ([6,6]-phenyl C71 butyric acid methyl ester). Besides, morphological studies have shown that a phase separation of 20–30 nm can only be observed in the SQ-EP/PC71BM blend film. Consequently, a solution-processed bulk-heterojunction (BHJ) organic photovoltaic (OPV) device fabricated with the as-cast SQ-EP/PC71BM blend film exhibited obviously higher power conversion efficiency (PCE: 5.4%) than those of the SQ-EN/PC71BM (PCE: 4.3%) or SQ-EF/PC71BM systems (PCE: 2.8%). This is one of the highest recorded PCE values in aniline-based squaraines single-junction BHJ-OPV devices. This much-enhanced PCE can be attributed to the significant increases in short-circuit current density (Jsc) and fill factor (FF) of the SQ-EP/PC71BM-based OPV device.
Nickel-Catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study
Bismuto, Alessandro,Delcaillau, Tristan,Müller, Patrick,Morandi, Bill
, p. 4630 - 4639 (2020/05/19)
Herein, we report a nickel-1,2-bis(dicyclohexylphosphino)ethane (dcype) complex for the catalytic Buchwald-Hartwig amination of aryl thioethers. The protocol shows broad applicability with a variety of different functional groups tolerated under the catalytic conditions. Extensive organometallic and kinetic studies support a nickel(0)-nickel(II) pathway for this transformation and revealed the oxidative addition complex as the resting state of the catalytic cycle. All the isolated intermediates have proven to be catalytically and kinetically competent catalysts for this transformation. The fleeting transmetalation intermediate has been successfully synthesized through an alternative synthetic organometallic pathway at lower temperature, allowing for in situ NMR study of the C-N bond reductive elimination step. This study addresses key factors governing the mechanism of the nickel-catalyzed Buchwald-Hartwig amination process, thus improving the understanding of this important class of reactions.
Catalytic Selective Oxidative Coupling of Secondary N-Alkylanilines: An Approach to Azoxyarene
Ke, Lei,Zhu, Guirong,Qian, Hui,Xiang, Guangya,Chen, Qin,Chen, Zhilong
supporting information, p. 4008 - 4013 (2019/06/04)
Azoxyarenes are among important scaffolds in organic molecules. Direct oxidative coupling of primary anilines provides a concise fashion to construct them. However, whether these scaffolds can be prepared from secondary N-alkylanilines is not well explored. Here, we present a catalytic selective oxidative coupling of secondary N-alkylaniline to afford azoxyarene with tungsten catalyst under mild conditions. In addition, azoxy can be viewed as a bioisostere of alkene and amide. Several "azoxyarene analogues" of the corresponding bioactive alkenes and amides showed comparable promising anticancer activities.
Use of a Cyclometalated Iridium(III) Complex Containing a N∧C∧N-Coordinating Terdentate Ligand as a Catalyst for the α-Alkylation of Ketones and N-Alkylation of Amines with Alcohols
Liu, Pengcheng,Liang, Ran,Lu, Lei,Yu, Zhentao,Li, Feng
, p. 1943 - 1950 (2017/02/26)
A cyclometalated iridium(III) complex containing a N∧C∧N-coordinating terdentate ligand [Ir(dpyx-N,C,N)Cl(μ-Cl)]2 was found to be a general and highly effective catalyst for the α-alkylation of ketones and N-alkylation of amines with alcohols. In the presence of catalyst (1 mol % Ir) and base (0.2-0.5 equiv), a variety of desirable products were obtained in good yields under an air atmosphere. Notably, this research exhibited the new potential of Ir(III) complexes bearing non-Cp? ligand and will facilitate the progress of the hydrogen autotransfer process.
New squarylium derivative, and organic thin-film solar cell (by machine translation)
-
Paragraph 0037, (2017/05/18)
[A] without changing the energy level, improving the carrier mobility of a thin film state, and further improve the fill factor (FF) new squarylium derivative of improving energy conversion efficiency. Also, the novel squarylium derivative of donor material and organic thin film solar cell. [Solution] A compound represented by general formula (1) squarylium derivative;(In the general formula (1), R1 Are each independently an aromatic group, R2 The carbon number of 4 or more branched aliphatic hydrocarbon group independently. )[Drawing] no (by machine translation)
Formal Direct Cross-Coupling of Phenols with Amines
Chen, Zhengwang,Zeng, Huiying,Girard, Simon A.,Wang, Feng,Chen, Ning,Li, Chao-Jun
supporting information, p. 14487 - 14491 (2016/01/25)
The transition-metal-catalyzed amination of aryl halides has been the most powerful method for the formation of aryl amines over the past decades. Phenols are regarded as ideal alternatives to aryl halides as coupling partners in cross-couplings. An efficient palladium-catalyzed formal cross-coupling of phenols with various amines and anilines has now been developed. A variety of substituted phenols were compatible with the standard reaction conditions. Secondary and tertiary aryl amines could thus be synthesized in moderate to excellent yields.
