Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation.

Room temperature decarboxylative cyanation of carboxylic acids using photoredox catalysis and cyanobenziodoxolones: a divergent mechanism compared to alkynylation† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6sc04907a Click here for additional data file.

Room-temperature decarboxylative alkynylation of carboxylic acids using photoredox catalysis and EBX reagents.

Alkynes are used as building blocks in synthetic and medicinal chemistry, chemical biology, and materials science. Therefore, efficient methods for their synthesis are the subject of intensive research. Herein, we report the direct synthesis of alkynes from readily available carboxylic acids at room temperature under visible-light irradiation. The combination of an iridium photocatalyst with et...

Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis.

A visible-light-induced decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed. The corresponding trifluoromethylated alkenes were obtained in moderate to high yields with excellent functional group tolerance at ambient temperature. Preliminary mechanistic analyses suggest a radical-type mechanism.

Merging Photoredox with Copper Catalysis: Decarboxylative Alkynylation of α-Amino Acid Derivatives.

A novel and efficient decarboxylative alkynylation of N-(acetoxy)phthalimides of α-amino acids with terminal alkynes has been developed by merging photoredox with copper catalysis at room temperature, and the reaction provided the valuable propargylamines in good to excellent yields with assistance of [Ru(bpy)3]Cl2/CuI and visible light. The simple protocol, mild reaction conditions, and high e...

Transition-metal-free visible-light photoredox catalysis at room-temperature for decarboxylative fluorination of aliphatic carboxylic acids by organic dyes.

We report herein an efficient, general and green method for decarboxylative fluorination of aliphatic carboxylic acids. By using a transition-metal-free, organocatalytic photoredox system, the reaction of various aliphatic carboxylic acids with the Selectfluor reagent afforded the corresponding alkyl fluorides in satisfactory yields under visible light irradiation at room temperature.