Room-Temperature Carbon Isotope Exchange of Carboxylic Acids Through Photoredox Catalysis

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.

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

10.26434/chemrxiv.13111505.v1 ◽

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.

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ChemInform Abstract: Room Temperature Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids by Photoredox Catalysis.

ChemInform ◽

10.1002/chin.201424064 ◽

2014 ◽

Vol 45 (24) ◽

pp. no-no

Author(s):

Pan Xu ◽

Ablimit Abdukader ◽

Kaidong Hu ◽

Yixiang Cheng ◽

Chengjian Zhu

Keyword(s):

Carboxylic Acids ◽

Room Temperature ◽

Photoredox Catalysis ◽

Unsaturated Carboxylic Acids

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

Chemical Communications ◽

10.1039/c3cc48598f ◽

2014 ◽

Vol 50 (18) ◽

pp. 2308-2310 ◽

Cited By ~ 104

Author(s):

Pan Xu ◽

Ablimit Abdukader ◽

Kaidong Hu ◽

Yixiang Cheng ◽

Chengjian Zhu

Keyword(s):

Visible Light ◽

Carboxylic Acids ◽

Room Temperature ◽

Photoredox Catalysis ◽

Unsaturated Carboxylic Acids

A visible-light-induced decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids, which uses the Togni reagent as the CF3 source is disclosed.

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Metal-Free Regioselective Alkylation of Imidazo[1,2-a]pyridines with N-Hydroxyphthalimide Esters under Organic Photoredox Catalysis

Synlett ◽

10.1055/s-0039-1691567 ◽

2020 ◽

Vol 31 (04) ◽

pp. 363-368 ◽

Cited By ~ 4

Author(s):

Can Jin ◽

Bin Sun ◽

Tengwei Xu ◽

Liang Zhang ◽

Rui Zhu ◽

...

Keyword(s):

Visible Light ◽

Carboxylic Acids ◽

Room Temperature ◽

Eosin Y ◽

Photoredox Catalysis ◽

Mechanistic Studies ◽

Metal Free ◽

Regioselective Alkylation ◽

Decarboxylative Coupling ◽

Aliphatic Carboxylic Acids

A visible-light-induced direct C–H alkylation of imidazo[1,2-a]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N-hydroxyphthalimide (NHP) esters as alkylation reagents. A variety of NHP esters derived from aliphatic carboxylic acids (primary, secondary, and tertiary) were tolerated in this protocol, giving the corresponding C-5-alkylated products in moderate to excellent yields. Mechanistic studies indicate that a radical decarboxylative coupling pathway was involved in this process.

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