Easy Access to Drug Building-Blocks through Benzylic C-H Functionalization of Phenolic Ethers by Photoredox Catalysis

2021 ◽  
Author(s):  
Tobias Brandhofer ◽  
Martin Stinglhamer ◽  
Volker Derdau ◽  
Maria Mendez-Perez ◽  
Christoph Pöverlein ◽  
...  
Keyword(s):  
Visible Light ◽  
Radical Cation ◽  
Building Blocks ◽  
Easy Access ◽  
Photoredox Catalysis ◽  
Bond Forming

A visible light-mediated photocatalyzed C-C-bond forming method for the benzylic C-H functionalization of phenolether containing synthetic building blocks based on a radical-cation/deprotonation strategy is reported. This method allows the mild,...

Dual copper- and photoredox-catalysed C(sp2)–C(sp3) coupling

2019 ◽  
Vol 55 (29) ◽  
pp. 4238-4241 ◽  
Author(s):  
Euan B. McLean ◽  
Vincent Gauchot ◽  
Sebastian Brunen ◽  
David J. Burns ◽  
Ai-Lan Lee
Keyword(s):  
Visible Light ◽  
Boronic Acids ◽  
Copper Catalysis ◽  
Photoredox Catalysis ◽  
Bond Forming ◽  
Bond Forming Reactions

The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C–C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)–C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

scholarly journals α-Functionalization of Imines via Visible Light Photoredox Catalysis

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 562 ◽  
Author(s):  
Alberto F. Garrido-Castro ◽  
M. Carmen Maestro ◽  
José Alemán
Keyword(s):  
Visible Light ◽  
Building Blocks ◽  
Single Electron ◽  
Synthetic Chemistry ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Radical Intermediates ◽  
Research Programs ◽  
Electron Reduction

The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.

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

scholarly journals First use of a divalent lanthanide for visible-light-promoted photoredox catalysis

2018 ◽  
Vol 9 (5) ◽  
pp. 1273-1278 ◽  
Author(s):  
Tyler C. Jenks ◽  
Matthew D. Bailey ◽  
Jessica L. Hovey ◽  
Shanilke Fernando ◽  
Gihan Basnayake ◽  
...  
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Bond Forming ◽  
Divalent Europium ◽  
Bond Forming Reactions ◽  
Divalent Lanthanide

Divalent europium is used catalytically in visible-light-promoted photoredox bond-forming reactions.

Radical‐Cation Cascade to Aryltetralin Cyclic Ether Lignans Under Visible‐Light Photoredox Catalysis

2020 ◽  
Vol 132 (47) ◽  
pp. 21381-21388
Author(s):  
Jia‐Chen Xiang ◽  
Qian Wang ◽  
Jieping Zhu
Keyword(s):  
Visible Light ◽  
Radical Cation ◽  
Cyclic Ether ◽  
Photoredox Catalysis

Visible-Light-Induced Photoredox Catalysis: An Easy Access to Green Radical Chemistry

Synlett ◽  
2013 ◽  
Vol 24 (19) ◽  
pp. 2492-2505 ◽  
Author(s):  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Visible Light ◽  
Easy Access ◽  
Photoredox Catalysis ◽  
Radical Chemistry

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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