1383116-17-3

Upstream product

• 162648-31-9 1-benzoyl-4-methylpiperidine-4-carboxylic acid 
• 5274-99-7 1-benzoylisonipecotic acid 
• 498-94-2 isonipecotic acid 
• 98-88-4 benzoyl chloride 
• 19980-01-9 (4-hydroxy-4-methylpiperidin-1-yl)(phenyl)methanone 

Relevant academic research and scientific papers

One-pot synthesis of tertiary alkyl fluorides from methyl oxalates by radical deoxyfluorination under photoredox catalysis

Tertiary alkyl fluorides have been prepared from methyl oxalates derived from tertiary alcohols by a sequential one-pot hydrolysis/photoredox catalyzed radical deoxyfluorination sequence. The reaction operates under mild conditions and tolerates a wide range of functional groups. This method provides an alternative approach to ionic deoxyfluorination transformations for the incorporation of Carbone–Fluorine quaternary centers into organic molecules.

Synthesis of Alkyl Fluorides by Silver-Catalyzed Radical Decarboxylative Fluorination of Cesium Oxalates

A combination of silver nitrate (AgNO3) catalyst and Selectfluor was found to perform radical deoxyfluorination of cesium oxalates derived from corresponding alcohols. The reaction tolerates a wide range of functional groups and provides preferentially access to tertiary alkyl fluorides.

DECARBOXYLATIVE CROSS-COUPLING AND APPLICATIONS THEREOF

Methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. For example, methods described herein enable the production of numerous molecular species through decarboxylative cross-coupling via use of photoredox and transition metal catalysts. A method described herein, in some embodiments, comprises providing a reaction mixture including a photoredox catalyst, a transition metal catalyst, a coupling partner and a substrate having a carboxyl group. The reaction mixture is irradiated with a radiation source resulting in cross-coupling of the substrate and coupling partner via a mechanism including decarboxylation, wherein the coupling partner is selected from the group consisting of a substituted aromatic compound and a substituted aliphatic compound.

Decarboxylative fluorination of aliphatic carboxylic acids via photoredox catalysis

The direct conversion of aliphatic carboxylic acids to the corresponding alkyl fluorides has been achieved via visible light-promoted photoredox catalysis. This operationally simple, redox-neutral fluorination method is amenable to a wide variety of carboxylic acids. Photon-induced oxidation of carboxylates leads to the formation of carboxyl radicals, which upon rapid CO2-extrusion and F? transfer from a fluorinating reagent yield the desired fluoroalkanes with high efficiency. Experimental evidence indicates that an oxidative quenching pathway is operable in this broadly applicable fluorination protocol.

Silver-catalyzed decarboxylative fluorination of aliphatic carboxylic acids in aqueous solution

Although fluorinated compounds have found widespread applications in the chemical and materials industries, general and site-specific C(sp3)-F bond formations are still a challenging task. We report here that with the catalysis of AgNO3, various aliphatic carboxylic acids undergo efficient decarboxylative fluorination with SELECTFLUOR reagent in aqueous solution, leading to the synthesis of the corresponding alkyl fluorides in satisfactory yields under mild conditions. This radical fluorination method is not only efficient and general but also chemoselective and functional-group- compatible, thus making it highly practical in the synthesis of fluorinated molecules. A mechanism involvinig Ag(III)-mediated single electron transfer followed by fluorine atom transfer is proposed for this catalytic fluorodecarboxylation.