scholarly journals Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1054
Author(s):  
Xiao-Qiang Hu ◽  
Zi-Kui Liu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Efficient Synthesis ◽  
Acyl Radical ◽  
Acyl Chlorides ◽  
Aryl Radicals ◽  
Keto Acids ◽  
Acyl Radicals ◽  
Different Types ◽  
The Impact ◽  
Visible Light Photocatalytic

Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.

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 Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals

2013 ◽  
Vol 355 (8) ◽  
pp. 1477-1482 ◽  
Author(s):  
Simon Donck ◽  
Abdulkader Baroudi ◽  
Louis Fensterbank ◽  
Jean-Philippe Goddard ◽  
Cyril Ollivier
Keyword(s):  
Visible Light ◽  
Photocatalytic Reduction ◽  
Sulfonium Salts ◽  
Aryl Radicals ◽  
Visible Light Photocatalytic

Acyl Radicals from α-Keto Acids: Metal-Free Visible-Light-Promoted Acylation of Heterocycles

2021 ◽  
Author(s):  
Hu-Lin Zhu ◽  
Fan-Lin Zeng ◽  
Xiao-Lan Chen ◽  
Kai Sun ◽  
Hao-Cong Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Metal Free ◽  
Keto Acids ◽  
Acyl Radicals

ChemInform Abstract: Visible-Light Photocatalytic Reduction of Sulfonium Salts as a Source of Aryl Radicals.

ChemInform ◽  
2013 ◽  
Vol 44 (42) ◽  
pp. no-no
Author(s):  
Simon Donck ◽  
Abdulkader Baroudi ◽  
Louis Fensterbank ◽  
Jean-Philippe Goddard ◽  
Cyril Ollivier
Keyword(s):  
Visible Light ◽  
Photocatalytic Reduction ◽  
Sulfonium Salts ◽  
Aryl Radicals ◽  
Visible Light Photocatalytic

Visible-light-promoted acyl radical cascade reaction for accessing acylated isoquinoline-1,3(2H,4H)-dione derivatives

2020 ◽  
Vol 18 (10) ◽  
pp. 1940-1948 ◽  
Author(s):  
Yingpeng Su ◽  
Rong Zhang ◽  
Wenxuan Xue ◽  
Xuan Liu ◽  
Yanan Zhao ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Acyl Radical ◽  
Keto Acids ◽  
Radical Cascade

A visible-light-promoted radical acylation/cyclization cascade reaction of N-methacryloylbenzamides with α-keto acids was developed to construct acylated isoquinoline-dione derivatives.

scholarly journals NHCs and Visible Light-mediated Photoredox Co-catalyzed Radical 1,2-Dicarbonylation of Alkenes for 1,4-Diketones

2021 ◽  
Author(s):  
Lihong Wang ◽  
Jiaqiong Sun ◽  
Jiuli Xia ◽  
Mingrui Li ◽  
Lianjin Zhang ◽  
...  
Keyword(s):  
Value Added ◽  
Direct Access ◽  
Acyl Radical ◽  
Reaction Conditions ◽  
Ketyl Radical ◽  
Alkyl Radicals ◽  
Keto Acids ◽  
Acyl Radicals ◽  
Quenching Process ◽  
Selectivity Control

Alkenes are ubiquitous, and radical difunctionalization of alkenes represents one of the most practical approaches to constructing value-added compounds. Dicarbonylation of alkenes provides direct access to value-added 1,4-dicarbonyl compounds. However, selectivity control for unsymmetric 1,2-dicarbonylation is an unclosed challenge. We herein describe NHCs and photocatalysis co-catalyzed three competent radical 1,2-dicarbonylation of alkenes by distinguishing two carbonyl groups, providing structurally diversified 1,4-diketones. Mechanistic studies indicated that NHCs-stabilized ketyl-type radicals originate from aroyl fluorides via oxidative quenching process of excited photocatalysis, and acyl radicals are generated from single-electron-oxidation of α-keto acids. Distinct properties of acyl radical and NHCs-stabilized ketyl radical contributed to selectivity control. Transient acyl radicals are rapidly added to alkenes delivering alkyl radicals, which undergo subsequent radical-radical cross-coupling with ketyl-type radicals, affording 1,2-dicarbonylation products. This transformation features mild reaction conditions, broad substruct scope, and excellent selectivity, providing a general and practical approach for the dicarbonylation of olefins.

Catalyst-Free Generation of Acyl Radicals Induced by Visible Light in Water to Construct C-N Bonds

2021 ◽  
Author(s):  
Maogang Ran ◽  
Jiaxin He ◽  
Boyu Yan ◽  
Wenbo Liu ◽  
Yi Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Acyl Radical ◽  
Selective Conversion ◽  
Catalyst Free ◽  
Acyl Radicals ◽  
Free Generation ◽  
Direct Generation

We describe herein a catalyst-free and redox-neutral photochemical strategy for the direct generation of acyl radical from α-diketones, and its selective conversion of nitrosoarenes to hydroxyamide or amides with AcOH...

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