Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis

2015 ◽  
Vol 54 (38) ◽  
pp. 11196-11199 ◽  
Author(s):  
Quan-Quan Zhou ◽  
Wei Guo ◽  
Wei Ding ◽  
Xiong Wu ◽  
Xi Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Photoredox Catalysis

scholarly journals Acyl Radicals from Aromatic Carboxylic Acids by Means of Visible-Light Photoredox Catalysis

2015 ◽  
Vol 127 (47) ◽  
pp. 14272-14275 ◽  
Author(s):  
Giulia Bergonzini ◽  
Carlo Cassani ◽  
Carl-Johan Wallentin
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Photoredox Catalysis ◽  
Aromatic Carboxylic Acids ◽  
Acyl Radicals

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

2014 ◽  
Vol 50 (18) ◽  
pp. 2308-2310 ◽  
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.

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

Synlett ◽  
2020 ◽  
Vol 31 (04) ◽  
pp. 363-368 ◽  
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.

scholarly journals Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals

2017 ◽  
Vol 8 (5) ◽  
pp. 3618-3622 ◽  
Author(s):  
L. Candish ◽  
M. Freitag ◽  
T. Gensch ◽  
F. Glorius
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Radical Formation ◽  
Photoredox Catalysis ◽  
Aryl Radical ◽  
Aryl Radicals

Herein we present the first example of aryl radical formation via the visible light-mediated decarboxylation of aryl carboxylic acids using photoredox catalysis.

ChemInform Abstract: Decarboxylative Alkynylation and Carbonylative Alkynylation of Carboxylic Acids Enabled by Visible-Light Photoredox Catalysis.

ChemInform ◽  
2016 ◽  
Vol 47 (6) ◽  
pp. no-no
Author(s):  
Quan-Quan Zhou ◽  
Wei Guo ◽  
Wei Ding ◽  
Xiong Wu ◽  
Xi Chen ◽  
...  
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Photoredox Catalysis

Cooperative iodine and photoredox catalysis for direct oxidative lactonization of carboxylic acids

2019 ◽  
Vol 55 (7) ◽  
pp. 933-936 ◽  
Author(s):  
Thomas Duhamel ◽  
Kilian Muñiz
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Molecular Iodine ◽  
Organic Dye ◽  
Photoredox Catalysis ◽  
Cooperative Catalysis

C–H lactonization is enabled by visible light-promoted cooperative catalysis combining molecular iodine and an organic dye.

scholarly journals Stereoselective Synthesis of Unnatural α-Amino Acids through Photoredox Catalysis

2020 ◽  
Author(s):  
Andrey Shatskiy ◽  
Anton Axelsson ◽  
Björn Blomkvist ◽  
Jian-Quan Liu ◽  
Peter Dinér ◽  
...  
Keyword(s):  
Amino Acids ◽  
Dft Calculations ◽  
Visible Light ◽  
Carboxylic Acids ◽  
Convenient Method ◽  
Stereoselective Synthesis ◽  
Catalytic Amount ◽  
Radical Addition ◽  
Photoredox Catalysis ◽  
Acid Radical

A protocol for stereoselective C-radical addition to a chiral glyoxylate-derived sulfinyl imine was developed through visible light-promoted photoredox catalysis, providing a convenient method for the synthesis of unnatural α-amino acids. The developed protocol allows the use of ubiquitous carboxylic acids as radical precursors without prior derivatization. The protocol utilizes near-stoichiometric amounts of the imine and the acid radical precursor in combination with a catalytic amount of an organic acridinium-based photocatalyst. The mechanism for the developed transformation is discussed and the stereodetermining radical addition step was studied by the DFT calculations.

scholarly journals Acyl Radical Chemistry via Visible-Light Photoredox Catalysis

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 303-333 ◽  
Author(s):  
Ming-Yu Ngai ◽  
Arghya Banerjee ◽  
Zhen Lei
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Easy Access ◽  
Hypervalent Iodine ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Diverse Range ◽  
Acyl Chlorides ◽  
Keto Acids ◽  
Acyl Radicals

Visible-light photoredox catalysis enables easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-keto acids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes the recent progress on visible-light-driven acyl radical generation using transition-metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts.1 Introduction2 The Scope of This Review3 Aldehydes as a Source of Acyl Radicals4 α-Keto Acids as a Source of Acyl Radicals5 Carboxylic Acids as a Source of Acyl Radicals6 Anhydrides as a Source of Acyl Radicals7 Acyl Thioesters as a Source of Acyl Radicals8 Acyl Chlorides as a Source of Acyl Radicals9 Acyl Silanes as a Source of Acyl Radicals10 Conclusions and Future Outlook

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