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 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 Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation

2021 ◽  
Author(s):  
Minghao Feng ◽  
Joao De Oliveira ◽  
Antoine Sallustrau ◽  
Gianluca Destro ◽  
Pierre Thuéry ◽  
...  
Keyword(s):  
Carbon Isotope ◽  
Isotope Exchange ◽  
Organic Molecules ◽  
Safety Evaluation ◽  
Single Step ◽  
Pharmaceutical Development ◽  
Structural Modifications ◽  
Carbon 14 ◽  
Metal Catalyzed ◽  
Food Safety Evaluation

The incorporation of carbon-14 allows tracking of organic molecules and provides vital knowledge on their fate. This information is critical in pharmaceutical development, crop science and human food safety evaluation. Herein, a transition-metal-catalyzed procedure enabling carbon isotope exchange on aromatic nitriles is described. Utilizing the radiolabeled precursor Zn([<sup>14</sup>C]CN)<sub>2</sub>, this protocol allows the insertion of the desired carbon tag without need of structural modifications, in a single step. Reducing synthetic costs and limiting the generation of radioactive waste, this procedure will facilitate the labeling of nitrile containing drugs and accelerate <sup>14</sup>C-based ADME studies supporting drug development.

scholarly journals Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation

2021 ◽  
Author(s):  
Minghao Feng ◽  
Joao De Oliveira ◽  
Antoine Sallustrau ◽  
Gianluca Destro ◽  
Pierre Thuéry ◽  
...  
Keyword(s):  
Carbon Isotope ◽  
Isotope Exchange ◽  
Organic Molecules ◽  
Safety Evaluation ◽  
Single Step ◽  
Pharmaceutical Development ◽  
Structural Modifications ◽  
Carbon 14 ◽  
Metal Catalyzed ◽  
Food Safety Evaluation

The incorporation of carbon-14 allows tracking of organic molecules and provides vital knowledge on their fate. This information is critical in pharmaceutical development, crop science and human food safety evaluation. Herein, a transition-metal-catalyzed procedure enabling carbon isotope exchange on aromatic nitriles is described. Utilizing the radiolabeled precursor Zn([<sup>14</sup>C]CN)<sub>2</sub>, this protocol allows the insertion of the desired carbon tag without need of structural modifications, in a single step. Reducing synthetic costs and limiting the generation of radioactive waste, this procedure will facilitate the labeling of nitrile containing drugs and accelerate <sup>14</sup>C-based ADME studies supporting drug development.

scholarly journals Transition‐Metal‐Free Carbon Isotope Exchange of Phenyl Acetic Acids

2020 ◽  
Vol 132 (32) ◽  
pp. 13592-13597
Author(s):  
Gianluca Destro ◽  
Kaisa Horkka ◽  
Olivier Loreau ◽  
David‐Alexandre Buisson ◽  
Lee Kingston ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbon Isotope ◽  
Isotope Exchange ◽  
Free Carbon ◽  
Metal Free ◽  
Acetic Acids

scholarly journals Transition‐Metal‐Free Carbon Isotope Exchange of Phenyl Acetic Acids

2020 ◽  
Vol 59 (32) ◽  
pp. 13490-13495 ◽  
Author(s):  
Gianluca Destro ◽  
Kaisa Horkka ◽  
Olivier Loreau ◽  
David‐Alexandre Buisson ◽  
Lee Kingston ◽  
...  
Keyword(s):  
Transition Metal ◽  
Carbon Isotope ◽  
Isotope Exchange ◽  
Free Carbon ◽  
Metal Free ◽  
Acetic Acids

The effect of decationation of hydroxylated HNaY zeolites on their interaction with ethylene and propylene. hydrogen complexes, oligomeration and isotope exchange

1980 ◽  
Vol 45 (11) ◽  
pp. 3101-3115 ◽  
Author(s):  
Ludmila Kubelková ◽  
Jana Nováková ◽  
Zdeněk Dolejšek ◽  
Pavel Jírů
Keyword(s):  
Isotope Exchange ◽  
Decisive Role ◽  
Single Step ◽  
Hydroxyl Groups ◽  
Isotope Exchange Reaction ◽  
Factors Affecting ◽  
Step Mechanism ◽  
Formed Hydrogen ◽  
Lower Basicity ◽  
Multiple Step

The effect of decationation on the interaction of propylene and ethylene with the hydroxylated forms of HNaY zeolites has been studied. The compounds formed in the zeolite cavities were studied using their infrared spectra, the composition of the gaseous phase was followed by mass spectrometry. The results showed that among factors affecting the interaction with propylene properties of hydroxyl groups play the decisive role. With the increasing decationation of the zeolite the strength of the OH bond in the hydrogen complex of the large-cavity hydroxyls with propylene decreased and the rate of propylene oligomeration at 310 K as well as the isotope exchange rate of propylene-d6 with the zeolite hydroxyls at 570 K increased. The propylene isotope exchange reaction proceeded by the multiple-step mechanism. In the case of ethylene only the physical sorption with a non-specific character was observed at 310 K. The adsorbed amount increased with the increasing content of Na+ ions in the zeolite (with the decreasing decationation). A part of the adsorbed molecules formed hydrogen complexes with hydroxyls of large cavities. The observed lower weakening of the OH bond was in agreement with the lower basicity of ethylene if compared with propylene. The isotope exchange of ethylene-d4 with the zeolite hydroxyls proceeded by a single-step mechanism, it had an autocatalytic character and its rate was 70 times lower than that of the isotope exchange of propylene-d6 with OH.

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 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 H/D Exchange Under Mild Conditions in Arenes and Unactivated Alkanes with C6D6 and D2O Using Rigid, Electron-rich Iridium PCP Pincer Complexes

2020 ◽  
Author(s):  
Joel D. Smith ◽  
George Durrant ◽  
Daniel Ess ◽  
Warren Piers
Keyword(s):  
Hydrogen Isotope ◽  
Isotope Exchange ◽  
Room Temperature ◽  
Pincer Complexes ◽  
Synthesis And Characterization ◽  
Hydrogen Isotope Exchange ◽  
Mild Conditions ◽  
Highly Active ◽  
Pcp Pincer

<div>The synthesis and characterization of an iridium polyhydride complex (Ir-H4)</div><div>supported by an electron-rich PCP framework is described. This complex readily loses molecular</div><div>hydrogen allowing for rapid room temperature hydrogen isotope exchange (HIE) at the hydridic</div><div>positions and the α-C-H site of the ligand with deuterated solvents such as benzene-d6, toluene-d8</div><div>and THF-d8. The removal of 1-2 equivalents of molecular H2 forms unsaturated iridium carbene</div><div>trihydride (Ir-H3) or monohydride (Ir-H) compounds that are able to create further unsaturation</div><div>by reversibly transferring a hydride to the ligand carbene carbon. These species are highly active</div><div>hydrogen isotope exchange (HIE) catalysts using C6D6 or D2O as deuterium sources for the</div><div>deuteration of a variety of substrates. By modifying conditions to influence the Ir-Hn speciation,</div><div>deuteration levels can range from near exhaustive to selective only for sterically accessible sites.</div><div>Preparative level deuterations of select substrates were performed allowing for procurement of</div><div>>95% deuterated compounds in excellent isolated yields; the catalyst can be regenerated by</div><div>treatment of residues with H2 and is still active for further reactions.</div>

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