9082-07-9 Purity
98%
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Specification
Cesium carbonate (Cs2CO3)-mediated cascade reaction can be used to synthesize dihydropyrrozinyl[3,2-b ]indol-10-one. The reaction mechanism involves sequential nucleophilic attacks of DMF with the enolate and pyrrolyl nitrogen, followed by the formation of transition metal-free C-N bonds.
Cesium carbonate-mediated cascade reaction procedure
· A sealed tube was charged with 2-(2-bromophenyl)-1-(N-tosyl-2-pyrrolyl)propan-1-one (1.0 mmol), Cs2CO3 (2.0 mmol) and DMF (10 mL).
· The reaction system was recharged with nitrogen three times. The reaction mixture was heated at 120 °C for 24 h and cooled.
· The mixture was partitioned between EtOAc (20 mL) and H2O (40 mL). The separated aqueous phase was extracted with EtOAc (3 × 20 mL).
· The combined organic extracts were washed with brine (100 mL), then dried (Na2SO4), filtered, and evaporated in vacuo. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford the products.
Cesium carbonate is an alkali metal carbonate with a wide range of applications and has been shown to be a mild inorganic base in organic synthesis. It has attracted much attention for its applications in C, N, O alkylation and arylation reactions. Cesium carbonate not only promotes successful carbonylation of alcohols and carbamate formation of amines, but also suppresses common side reactions traditionally encountered with other protocols. It is also used in six-membered cyclizations, intramolecular and intermolecular cyclizations, Suzuki couplings, aza-Henry, nucleophilic substitutions, cross-couplings, and different cycloaddition reactions.
α-Alkylation of ketones and amides is an important transformation for carbon-carbon bond formation and is widely used in the synthesis of natural products and bioactive compounds. Iridium complexes with functionalized bipyridyl ketone ligands are efficient catalysts for α-alkylation of ketones with primary alcohols under environmentally friendly and mild conditions in cesium carbonate. α-Alkylation of acetophenone with benzyl alcohol was used as a model reaction to study the effect of different iridium catalysts on the reaction yield. The reaction was carried out in the presence of Cs2CO3 (0.1 equiv per substrate) at 110 °C and in tert-amyl alcohol under reflux in air atmosphere to give α-alkylated products in varying yields. Many organic transformations may require the presence of cesium carbonate to promote expulsion and carbanion formation, as well as arylation and alkylation of alcohols, carboxylic acids, and amines. It has also been used for C-C bond formation, such as the Michael reaction.
The device characteristics of polymer solar cells with cesium carbonate Cs2CO3 as an electron injection interlayer were studied. It was found that the insertion of Cs2CO3 at the cathode interface can improve the device power conversion efficiency from 2.3% to 3.1%. To further understand its mechanism, the interfacial interaction between the active organic layer and the cathode was studied by X-ray photoelectron spectroscopy XPS. XPS measurements show that part of the electrons are transferred from the interlayer to the organic layer, resulting in n-type doping. The n-type doping effect improves the efficiency of electron injection and collection. In addition, the maximum open circuit voltage V is determined by its temperature dependence. For the device with Cs2CO3, the maximum Vi is extremely close to the corresponding value of the energy difference between the highest occupied molecular orbital of the electron donor and the lowest unoccupied molecular orbital of the electron acceptor, indicating a better ohmic contact. All evidence shows that Cs2CO3 is a promising candidate as an interlayer to improve device performance.
The ITO substrate was cleaned in an ultrasonic bath with detergent, acetone, and isopropanol in sequence, and finally rinsed with deionized water. After cleaning, the ITO glass was dried in an oven and then treated with UV ozone. A thin layer of poly (3,4-ethylenedioxythiophene): polystyrene sulfonate PEDOT:PPS) was covered on the cleaned substrate by spin coating and then baked at 120 °C for 60 min. An active layer with a weight ratio of P3HT:PCBM = 1:1 was spin coated on top of PEDOT:PSS from a 1.7 wt% 1,2-dichlorobenzene solution. The active film was thermally annealed at 110 °C for 15 min before depositing the cathode. To complete the device, a sandwich of Cs2CO3 1 nm and Al 100 nm was thermally evaporated by shadow mask, defining a device area of 0.12 cm2 under a vacuum of 6×10 Torr.
The molecular formula of Cesium Carbonate is Cs2CO3.
The molecular weight of Cesium Carbonate is 325.820 g/mol.
Cesium Carbonate was first created in 2005-07-19.
The IUPAC name of Cesium Carbonate is dicesium;carbonate.
The Canonical SMILES representation of Cesium Carbonate is C(=O)([O-])[O-].[Cs+].[Cs+].
Cesium Carbonate has 3 hydrogen bond acceptors.
The exact mass of Cesium Carbonate is 325.7956478 g/mol.
Cesium Carbonate has a topological polar surface area of 63.2?2.
Cesium Carbonate has 6 heavy atoms.
Cesium Carbonate has 0 defined atom stereocenter counts.