Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst

2019 ◽  
Vol 21 (19) ◽  
pp. 5368-5373 ◽  
Author(s):  
Hongshuo Jiang ◽  
Guijie Mao ◽  
Hongfeng Wu ◽  
Qi An ◽  
Minghui Zuo ◽  
...  
Keyword(s):  
Methylene Blue ◽  
Carboxylic Acids ◽  
Radical Cyclization ◽  
Cyclization Reaction ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Aromatic Carboxylic Acids

An efficient intramolecular radical cyclization reaction via photoredox catalysis was developed for the synthesis of dibenzocycloketone derivatives using methylene blue as a photosensitizer.

scholarly journals Correction: Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst

2020 ◽  
Vol 22 (4) ◽  
pp. 1443-1443
Author(s):  
Hongshuo Jiang ◽  
Guijie Mao ◽  
Hongfeng Wu ◽  
Qi An ◽  
Minghui Zuo ◽  
...  
Keyword(s):  
Methylene Blue ◽  
Carboxylic Acids ◽  
Radical Cyclization ◽  
Acyl Radical ◽  
Aromatic Carboxylic Acids

Correction for ‘Synthesis of dibenzocycloketones by acyl radical cyclization from aromatic carboxylic acids using methylene blue as a photocatalyst’ by Hongshuo Jiang et al., Green Chem., 2019, 21, 5368–5373.

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.

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

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.

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

Visible-Light-Promoted Synthesis of Pyrrolidinone Derivatives via Rose Bengal as a Photoredox Catalyst and Their Photophysical Studies

2021 ◽  
Author(s):  
Arup Dutta ◽  
Mostofa Ataur Rohman ◽  
Ridaphun Nongrum ◽  
Aiborlang Thongni ◽  
Sivaprasad Mitra ◽  
...  
Keyword(s):  
Visible Light ◽  
Rose Bengal ◽  
Radical Cyclization ◽  
Cyclization Reaction ◽  
Photoredox Catalysis ◽  
Blue Led ◽  
Metal Free ◽  
Photophysical Studies ◽  
Reaction Profile ◽  
Led Irradiation

An intramolecular radical cyclization reaction towards the synthesis of pyrrolidinone derivatives via metal free photoredox catalysis under blue LED irradiation has been reported. Synthetic efficiency, green reaction profile, easy isolation...

Photoredox/Nickel-Catalyzed Hydroacylation of Ethylene with Aromatic Acids

2021 ◽  
Author(s):  
Jin Xie ◽  
Lili Zhang ◽  
Shuai Chen ◽  
hengchi He ◽  
Weipeng Li ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Photoredox Catalysis ◽  
Aromatic Acids ◽  
Aromatic Carboxylic Acids ◽  
Synergistic Combination

We report a general, practical and scalable hydroacylation reaction of ethylene with aromatic carboxylic acids with the synergistic combination of nickel and photoredox catalysis. This strategy was achieved by converting...

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