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Witnessing the Birth of Directed Evolution of Stereoselective Enzymes as Catalysts in Organic Chemistry

Abstract This invited essay outlines how the idea of directed evolution of stereoselective enzymes was born and implemented experimentally at the Max-Planck-Institut für Kohlenforschung in Mülheim/Germany during the period 1994–1998, a time when Andreas Pfaltz was present in the Institute. As the new and sole director of the MPI, I initiated new research...

Furan synthesis via triplet sensitization of acceptor/acceptor diazoalkanes

Herein, we report on the photocatalytic reaction of acceptor/acceptor diazoalkanes with terminal alkynes. Experimental and computational studies suggest the formation of a key triplet carbene intermediate that undergoes an addition reaction to the alkyne followed by cyclization to give furan heterocycles (31 to 90% yield). This reaction was studied...

Insight into the Stereocontrol of DNA Polymerase‐Catalysed Reaction by Chiral Cobalt Complexes.

The front cover picture, provided by Li Wu and her co-workers, illustrates stereocontrol of DNA polymerase–catalysed reaction by chiral cobalt complexes, which might seem like “chiral environmental agents”. One chiral enantiomer of the cobalt complexes interacts with substrate-binding site of DNA polymerase, exhibiting inhibition or acceleration of...

Copper‐Catalyzed Acylhalogenation of 3‐Methylanthranils with Acid Halides: Synthesis of N‐(2‐(2‐Haloyl)phenyl)amides

A copper-catalyzed acylhalogenation reaction of 3-methylanthranils with acid halides, which utilizes the acyl halide as both the acylating and halogenating source, is described. This process involves N-O/C-H/C-X bond cleavages and C-N/C-X bond formations to furnish N-(2-(2-haloyl)phenyl)amides. Furthermore, this difunctional conversion using the N-O...

Direct Synthesis of Dialkylphosphites from White Phosphorus

Abstract Dialkyl phosphites (DAPIs), traditionally prepared from hazardous and corrosive PCl3, are the fundamental reactive starting materials used in organophosphorus chemistry. Here, a KBr-mediated synthesis of DAPIs involving P4, alcohols and water is presented. With the use of silica gel as the catalyst, oxone as the safe oxidant, industrially...

Transition‐Metal‐Free N‐Functionalization of Benzimidazoles and Related Azaheterocycles with α‐Acyloxy Sulfides

Abstract Direct N-functionalization of benzimidazoles and related azaheterocycles has been achieved using readily accessible α-acyloxy sulfides under transition metal-free conditions. In the presence of the base, potassium carbonate, a variety of N-functionalized azaheterocyclic compounds bearing an N-alkyl ester moiety were synthesized from corresponding...

Cu(I) Mediated Azidation of Halobenzenes, and Cu Catalysed Selective Azide Reduction to Corresponding Amines.

The front cover image illustrates the complex mixture of a selective copper-mediated reaction of a bromobenzene bearing a bromoalkanoyl chain to an amine-azide. It proceeds stepwise via a bis-azide intermediate and produces copper nanostructures simultaneously, which grow on the PTFE stirring bar. The copper in the reaction mixture is responsible for...

Synthesis of 1‐Aryl Isoquinolinones or o‐Diaryl Pyrimidines via Bismuth Triflate‐Mediated Intermolecular Annulation of Arylacetic Acids with Nitroarylaldehydes or Trimethoxybenzene in the Presence of Acetonitrile

Abstract In this article, bismuth triflate (Bi(OTf)3)-controlled intermolecular multi-component condensation of oxygenated arylacetic acids with electron-withdrawing nitroarylaldehydes or electron-donating trimethoxybenzene provide 1-aryl isoquinolinones or o-diaryl pyrimidines in acetonitrile at 60 °C. The uses of various metal triflates and reaction...

Rhodium(CAAC)‐Catalyzed Arene Hydrogenation of Benzo‐Fused N‐Heterocycles to Saturated Building Blocks with an all‐cis Configuration

Abstract Saturated carbo- and heterocyclic building blocks can be readily obtained by the hydrogenation of aromatic carbo- and heterocycles. Although a variety of methods have been established to accomplish this transformation for simple arenes, the hydrogenation of aromatic N-heterocycles is less explored. We herein report a diastereoselective arene...

Tandem Asymmetric Cycloaromatization/ Intramolecular Pictet‐Spengler‐Type Reaction. An Entry to Polycyclic Pyrroles

Abstract The asymmetric synthesis of tetracyclic pyrroles bearing a tetrasubstituted carbon stereocenter has been accomplished through a one-pot sequence that comprises a cross metathesis reaction followed by a tandem cycloisomerization/ intramolecular Pictet-Spengler-type reaction. This sequence took place on conveniently functionalized chiral amino...

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