scholarly journals Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis

2021 ◽  
Vol 143 (5) ◽  
pp. 2200-2206
Author(s):  
Duanyang Kong ◽  
Maxime Munch ◽  
Qiqige Qiqige ◽  
Christopher J. C. Cooze ◽  
Benjamin H. Rotstein ◽  
...  
Keyword(s):  
Carbon Isotope ◽  
Carboxylic Acids ◽  
Isotope Exchange ◽  
Photoredox Catalysis

scholarly journals Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis

2020 ◽  
Author(s):  
Duanyang Kong ◽  
Maxime Munch ◽  
Qiqige Qiqige ◽  
Christopher Cooze ◽  
Benjamin Rotstein ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbon Isotope ◽  
Carboxylic Acids ◽  
Isotope Exchange ◽  
Room Temperature ◽  
Reaction Times ◽  
Thermally Induced ◽  
Drug Molecules ◽  
Metal Catalyzed ◽  
Isotopic Incorporation

Carbazole/cyanobenzene photocatalysts promote the direct isotopic carboxylate exchange of C(sp3 )-acids with labelled CO2. Substrates that are not compatible with transition metal catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabelling of drug molecules and precursors with [11C]CO2 is demonstrated.

scholarly journals Fast Carbon Isotope Exchange of Carboxylic Acids Enabled by Organic Photoredox Catalysis

2020 ◽  
Author(s):  
Duanyang Kong ◽  
Maxime Munch ◽  
Qiqige Qiqige ◽  
Christopher Cooze ◽  
Benjamin Rotstein ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbon Isotope ◽  
Carboxylic Acids ◽  
Isotope Exchange ◽  
Room Temperature ◽  
Reaction Times ◽  
Thermally Induced ◽  
Drug Molecules ◽  
Metal Catalyzed ◽  
Isotopic Incorporation

Carbazole/cyanobenzene photocatalysts promote the direct isotopic carboxylate exchange of C(sp3 )-acids with labelled CO2. Substrates that are not compatible with transition metal catalyzed degradation-reconstruction approaches or prone to thermally induced reversible decarboxylation undergo isotopic incorporation at room temperature in short reaction times. The radiolabelling of drug molecules and precursors with [11C]CO2 is demonstrated.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Late-Stage Carbon Isotope Exchange of Aryl Nitriles through Ni-Catalyzed C–CN Bond Activation

2021 ◽  
Vol 143 (12) ◽  
pp. 4817-4823
Author(s):  
Sean W. Reilly ◽  
Yu-hong Lam ◽  
Sumei Ren ◽  
Neil A. Strotman
Keyword(s):  
Carbon Isotope ◽  
Late Stage ◽  
Isotope Exchange ◽  
Bond Activation ◽  
Aryl Nitriles

scholarly journals A Photochemical Strategy for Carbon Isotope Exchange with CO2

2020 ◽  
Author(s):  
Victor Babin ◽  
Alex Talbot ◽  
Alexandre Labiche ◽  
Gianluca Destro ◽  
Antonio Del Vecchio ◽  
...  
Keyword(s):  
Carbon Isotope ◽  
Isotope Exchange ◽  
Thermal Conditions ◽  
Single Step ◽  
Structural Modifications ◽  
Mild Conditions ◽  
Stark Contrast ◽  
Acetic Acids

A novel photocatalytic approach for carbon isotope exchange is reported. Utilizing [<sup>13</sup>C]CO<sub>2</sub> as primary C1 sources, this protocol allows the insertion of the desired carbon isotope into phenyl acetic acids without the need of structural modifications or pre-functionalization, in one single step. The exceptionally mild conditions required for this traceless transformation are in stark contrast with previous methods requiring the use of harsh thermal conditions.

scholarly journals Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

2020 ◽  
Author(s):  
Anna Davies ◽  
keegan fitzpatrick ◽  
Rick Betori ◽  
Karl Scheidt
Keyword(s):  
Carboxylic Acids ◽  
Late Stage ◽  
Pharmaceutical Compounds ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Electron Reduction

Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium <i>in situ</i> followed by a radical-radical coupling was made possible using merged NHC-photoredox catalysis. The utility of this protocol in synthesis was demonstrated in the late-stage functionalization of a variety of pharmaceutical compounds.

ChemInform Abstract: Decarboxylative Fluorination of Aliphatic Carboxylic Acids via Photoredox Catalysis.

ChemInform ◽  
2015 ◽  
Vol 46 (42) ◽  
pp. no-no
Author(s):  
Sandrine Ventre ◽  
Filip R. Petronijevic ◽  
David W. C. MacMillan
Keyword(s):  
Carboxylic Acids ◽  
Photoredox Catalysis ◽  
Aliphatic Carboxylic Acids

Timing and mechanisms of carbon isotope exchange in granulite-facies calc-silicate boudins, Rauer Group, East Antarctica

1997 ◽  
Vol 82 (3-4) ◽  
pp. 392-404 ◽  
Author(s):  
Ian Cartwright ◽  
Ian S. Buick ◽  
Simon L. Harley
Keyword(s):  
Carbon Isotope ◽  
Isotope Exchange ◽  
Granulite Facies ◽  
East Antarctica
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