A rational synthetic approach for producing quaternary ammonium halides and physical properties of the room temperature ionic liquids obtained by this way

In the present paper the rational strategy for the high-yield solvent free synthesis of alkylammonium halides which consists in the nucleophilic addition of alkylaminoethanols to 2-chloroethanol was described. The proposed strategy was used to synthesize hydroxyl-functionalized solid ionic compounds such as dimethyl (or methyl) di-(tri)(2-hydroxyethyl) ammonium chloride and tetra-(2-hydroxyethyl) ammonium chloride, as well as novel room temperature ionic liquids (RTILs) such as dimethyl (IL-4) and methyl mono-(di-)(2-hydroxyethyl) (2-hydroxyethoxy)ethyl chloride (IL-5) all of which were characterized by FT-IR, 1H and 13C NMR. For the newly obtained RTILs, density (ρ) and viscosity (η) were obtained at temperatures from T = (283.15 to 353.15) K while the refractive index (nD) was measured from T = (283.15 to 343.15) K. The data on ρ and nD were used for calculation of the RTILs’ fractional free volumes (FFV), molar refraction, and pseudo-activation energy of viscous flow. In addition, NH3 absorption capacity of the obtained ILs was estimated gravimetrically. It was shown that this property correlates with the IL's FFV and increases by two times for IL-5 which exhibits an additional hydroxyl group compared to IL-4

Mild and selective base-free C–H arylation of heteroarenes: experiment and computation

A mild and selective C–H arylation strategy for indoles, benzofurans and benzothiophenes is described. The arylation method engages aryldiazonium salts as arylating reagents in equimolar amounts. The protocol is operationally simple, base free, moisture tolerant and air tolerant. It utilizes low palladium loadings (0.5 to 2.0 mol% Pd), short reaction times, green solvents (EtOAc/2-MeTHF or MeOH) and is carried out at room temperature, providing a broad substrate scope (47 examples) and excellent selectivity (C-2 arylation for indoles and benzofurans, C-3 arylation for benzothiophenes). Mechanistic experiments and DFT calculations support a Heck–Matsuda type coupling mechanism.Hannes P.L. Gemoets, Indrek Kalvet, Alexander V. Nyuchev, Nico Erdmann, Volker Hessel, Franziska Schoenebeck and Timothy Noë

Decatungstate‐mediated C(sp3)‒H Heteroarylation via Radical‐Polar Crossover in Batch and Flow

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical-polar crossover concept to access the direct net-oxidative C(sp3)-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin, and dideoxyribose

Decatungstate-Mediated C(sp3)-H Heteroarylation via Radical-Polar Crossover in Batch and Flow

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical-polar crossover concept to access the direct net-oxidative C(sp3)-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin, and dideoxyribose

Decatungstate-Mediated C(sp3)-H Heteroarylation via Radical-Polar Crossover in Batch and Flow

Photocatalytic hydrogen atom transfer is a very powerful strategy for the regioselective C(sp3)-H functionalization of organic molecules. Herein, we report on the unprecedented combination of decatungstate hydrogen atom transfer photocatalysis with the oxidative radical-polar crossover concept to access the direct net-oxidative C(sp3)-H heteroarylation. The present methodology demonstrates a high functional group tolerance (40 examples) and is scalable when using continuous-flow reactor technology. The developed protocol is also amenable to the late-stage functionalization of biologically relevant molecules such as stanozolol, (-)-ambroxide, podophyllotoxin, and dideoxyribose

Modern Trends of Organic Chemistry in Russian Universities

This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade. © 2018, Pleiades Publishing, Ltd

Modern Trends of Organic Chemistry in Russian Universities

© 2018, Pleiades Publishing, Ltd. This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade

Modern Trends of Organic Chemistry in Russian Universities

This review is devoted to the scientific achievements of the departments of organic chemistry in higher schools of Russia within the past decade. © 2018, Pleiades Publishing, Ltd