scholarly journals Recent Advances in Visible-Light-Mediated Amide Synthesis

Molecules ◽  
2022 ◽  
Vol 27 (2) ◽  
pp. 517
Author(s):  
Bin Lu ◽  
Wen-Jing Xiao ◽  
Jia-Rong Chen
Keyword(s):  
Visible Light ◽  
Organic Molecules ◽  
Structural Motif ◽  
Radical Reactions ◽  
Photoredox Catalysis ◽  
Mild Conditions ◽  
Amide Synthesis ◽  
Functionalized Materials ◽  
Activating Agent ◽  
Ubiquitous Presence

Visible-light photoredox catalysis has attracted tremendous interest within the synthetic community. As such, the activation mode potentially provides a more sustainable and efficient platform for the activation of organic molecules, enabling the invention of many controlled radical-involved reactions under mild conditions. In this context, amide synthesis via the strategy of photoredox catalysis has received growing interest due to the ubiquitous presence of this structural motif in numerous natural products, pharmaceuticals and functionalized materials. Employing this strategy, a wide variety of amides can be prepared effectively from halides, arenes and even alkanes under irradiation of visible light. These methods provide a robust alternative to well-established strategies for amide synthesis that involve condensation between a carboxylic acid and amine mediated by a stoichiometric activating agent. In this review, the representative progresses made on the synthesis of amides through visible light-mediated radical reactions are summarized.

Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible Light Photoredox Catalysis

Synthesis ◽  
2020 ◽  
Author(s):  
Jia-Jia Zhao ◽  
Hong-Hao Zhang ◽  
Shouyun Yu
Keyword(s):  
Visible Light ◽  
Asymmetric Synthesis ◽  
Carbonyl Compounds ◽  
Asymmetric Reduction ◽  
Chemical Transformations ◽  
Photoredox Catalysis ◽  
Radical Coupling ◽  
Mild Conditions ◽  
Iminium Ions ◽  
Radical Functionalization

Visible light photoredox catalysis has recently emerged as a powerful tool for the development of new and valuable chemical transformations under mild conditions. Visible-light promoted enantioselective radical transformations of imines and iminium intermediates provide new opportunities for the asymmetric synthesis of amines and asymmetric β-functionalization of unsaturated carbonyl compounds. In this review, the advance in the catalytic asymmetric radical functionalization of imines, as well as iminium intermediates, are summarized. 1 Introduction 2 The enantioselective radical functionalization of imines 2.1 Asymmetric reduction 2.2 Asymmetric cyclization 2.3 Asymmetric addition 2.4 Asymmetric radical coupling 3 The enantioselective radical functionalization of iminium ions 3.1 Asymmetric radical alkylation 3.2 Asymmetric radical acylation 4 Conclusion

Three-component difluoroalkylation–thiolation of alkenes by iron-facilitated visible-light photoredox catalysis

2019 ◽  
Vol 55 (30) ◽  
pp. 4383-4386 ◽  
Author(s):  
Rui Xu ◽  
Chun Cai
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Mild Conditions

The first difluoroalkylation–thiolation of alkenes catalyzed by iron-facilitated photoredox has been developed with a broad substrate scope under mild conditions.

Visible Light Promoted Functionalisation of Carbon-Carbon Sigma Bonds

2019 ◽  
Author(s):  
Jeremy Nugent ◽  
Carlos Arroniz ◽  
Bethany Shire ◽  
Alistair J. Sterling ◽  
Helena D. Pickford ◽  
...  
Keyword(s):  
Visible Light ◽  
Organic Molecules ◽  
Functional Group ◽  
Single Step ◽  
Transition Metal Catalysts ◽  
Organic Radicals ◽  
Photoredox Catalysis ◽  
Halogen Bonds ◽  
Organic Halides ◽  
Pi Bonds

<p>The use of visible light to activate transition metal catalysts towards redox processes has transformed the way organic molecules can be constructed. Promotion of an electron to an excited state enables the generation of organic radicals through electron transfer to or from the metal complex, with the resulting radicals primed for reactions such as addition to carbon–carbon pi bonds. Despite advances in photoredox catalysis which have led to the discovery of numerous such methods for bond construction, this mild approach to the generation of free radicals has not been applied to the functionalisation of carbon–carbon sigma<i></i>bonds. Here we report the first such use of photoredox catalysis to promote the addition of organic halides to the caged carbocycle [1.1.1]propellane; the products of this process are bicyclo[1.1.1]pentanes (BCPs), motifs that are of high importance as bioisosteres in the pharmaceutical industry, and in materials applications. The methodology shows broad substrate scope and functional group tolerance, and is applicable to both <i>sp</i><sup>2</sup>and <i>sp</i><sup>3</sup>carbon–halogen bonds, while the use of substrates containing alkene acceptors enables the single-step construction of polycyclic bicyclopentane products through cyclisation cascades. Finally, the potential to accelerate drug discovery is demonstrated through examples of late-stage bicyclopentylation to access natural product- and drug-like molecules.</p>

Metal-free oxidative phosphinylation of aryl alkynes to β-ketophosphine oxides via visible-light photoredox catalysis

2016 ◽  
Vol 6 (2) ◽  
pp. 413-416 ◽  
Author(s):  
Mei-jie Bu ◽  
Guo-ping Lu ◽  
Chun Cai
Keyword(s):  
Visible Light ◽  
Organic Dye ◽  
Photoredox Catalysis ◽  
Metal Free ◽  
Mild Conditions ◽  
Aryl Alkynes

A visible-light-induced oxidative phosphinylation of arylacetylenes catalyzed by an inexpensive organic dye was demonstrated to be effective under mild conditions.

Visible Light Promoted Functionalisation of Carbon-Carbon Sigma Bonds

2019 ◽  
Author(s):  
Jeremy Nugent ◽  
Carlos Arroniz ◽  
Bethany Shire ◽  
Alistair J. Sterling ◽  
Helena D. Pickford ◽  
...  
Keyword(s):  
Visible Light ◽  
Organic Molecules ◽  
Functional Group ◽  
Single Step ◽  
Transition Metal Catalysts ◽  
Organic Radicals ◽  
Photoredox Catalysis ◽  
Halogen Bonds ◽  
Organic Halides ◽  
Pi Bonds

<p>The use of visible light to activate transition metal catalysts towards redox processes has transformed the way organic molecules can be constructed. Promotion of an electron to an excited state enables the generation of organic radicals through electron transfer to or from the metal complex, with the resulting radicals primed for reactions such as addition to carbon–carbon pi bonds. Despite advances in photoredox catalysis which have led to the discovery of numerous such methods for bond construction, this mild approach to the generation of free radicals has not been applied to the functionalisation of carbon–carbon sigma<i></i>bonds. Here we report the first such use of photoredox catalysis to promote the addition of organic halides to the caged carbocycle [1.1.1]propellane; the products of this process are bicyclo[1.1.1]pentanes (BCPs), motifs that are of high importance as bioisosteres in the pharmaceutical industry, and in materials applications. The methodology shows broad substrate scope and functional group tolerance, and is applicable to both <i>sp</i><sup>2</sup>and <i>sp</i><sup>3</sup>carbon–halogen bonds, while the use of substrates containing alkene acceptors enables the single-step construction of polycyclic bicyclopentane products through cyclisation cascades. Finally, the potential to accelerate drug discovery is demonstrated through examples of late-stage bicyclopentylation to access natural product- and drug-like molecules.</p>

Visible-light radical reaction designed by Ru- and Ir-based photoredox catalysis

2014 ◽  
Vol 1 (8) ◽  
pp. 562-576 ◽  
Author(s):  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Visible Light ◽  
Radical Reaction ◽  
Radical Reactions ◽  
Photoredox Catalysis

New and easy protocols for radical reactions have been developed.

scholarly journals α-Alkylation of ketimines using visible light photoredox catalysis

RSC Advances ◽  
2017 ◽  
Vol 7 (69) ◽  
pp. 43655-43659 ◽  
Author(s):  
Allegra Franchino ◽  
Antonia Rinaldi ◽  
Darren J. Dixon
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Mild Conditions

A novel α-alkylation of N-diphenylphosphinoyl ketimines with α-bromocarbonyl compounds has been accomplished under mild conditions using nickel and ruthenium light-promoted catalysis.

scholarly journals Photoredox catalysis by [Ru(bpy)3]2+ to trigger transformations of organic molecules. Organic synthesis using visible-light photocatalysis and its 20th century roots

2011 ◽  
Vol 76 (7) ◽  
pp. 859-917 ◽  
Author(s):  
Filip Teplý
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Organic Molecules ◽  
Recent Literature ◽  
Synthetic Methods ◽  
Bond Breaking ◽  
Materials Chemistry ◽  
Photoredox Catalysis ◽  
Contemporary Work ◽  
Developing Area

Reactions triggered by light constitute a treasure trove of unique synthetic methods that are available to chemists. Photoinduced redox processes using visible light in conjunction with sensitizing dyes offer a great variety of catalytic transformations useful in the realm of organic synthesis. The recent literature amply shows that this preparative toolbox is expanding substantially. This review discusses historical and contemporary work in the area of photoredox catalysis with [Ru(bpy)3]2+. Elegant examples from the most recent literature document the importance of this fast developing area of research. The photoredox chemistry has also emerged as a promising bond-making and bond-breaking tool for chemical biology and materials chemistry. A review with 96 references.

scholarly journals Application of visible-light photosensitization to form alkyl-radical-derived thin films on gold

2017 ◽  
Vol 8 ◽  
pp. 1863-1877 ◽  
Author(s):  
Rashanique D Quarels ◽  
Xianglin Zhai ◽  
Neepa Kuruppu ◽  
Jenny K Hedlund ◽  
Ashley A Ellsworth ◽  
...  
Keyword(s):  
Thin Films ◽  
Visible Light ◽  
Alkyl Radical ◽  
Organic Molecules ◽  
Film Structure ◽  
Small Organic Molecules ◽  
Alkyl Radicals ◽  
Mild Conditions ◽  
Radical Generation ◽  
First Time

Visible-light irradiation of phthalimide esters in the presence of the photosensitizer [Ru(bpy)3]2+ and the stoichiometric reducing agent benzyl nicotinamide results in the formation of alkyl radicals under mild conditions. This approach to radical generation has proven useful for the synthesis of small organic molecules. Herein, we demonstrate for the first time the visible-light photosensitized deposition of robust alkyl thin films on Au surfaces using phthalimide esters as the alkyl radical precursors. In particular, we combine visible-light photosensitization with particle lithography to produce nanostructured thin films, the thickness of which can be measured easily using AFM cursor profiles. Analysis with AFM demonstrated that the films are robust and resistant to mechanical force while contact angle goniometry suggests a multilayered and disordered film structure. Analysis with IRRAS, XPS, and TOF SIMS provides further insights.

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