Visible-light-induced selectivity controllable synthesis of diamine or imidazoline derivatives by multicomponent decarboxylative radical coupling reactions

2020 ◽  
Vol 7 (24) ◽  
pp. 4043-4049
Author(s):  
Shulei Pan ◽  
Min Jiang ◽  
Guofu Zhong ◽  
Linlong Dai ◽  
Yu Zhou ◽  
...  
Keyword(s):  
Visible Light ◽  
Coupling Reactions ◽  
Controllable Synthesis ◽  
Reaction Conditions ◽  
Radical Coupling ◽  
Imidazoline Derivatives ◽  
Vicinal Diamines

A visible-light-induced and photoredox-catalyzed three-component selectivity controllable synthesis of vicinal diamines and imidazoles from readily available starting materials under mild reaction conditions has been realized.

scholarly journals Visible-Light-Induced Oxidative Cleavage of C-C Triple Bond via Hydroamination: Direct Synthesis of Oxamates from Amines and Activated Alkynes

2019 ◽  
Author(s):  
Sharada Duddu. S ◽  
Sagar Arepally ◽  
Arumugavel Murugan ◽  
Narenderreddy Katta ◽  
Mamata Ojha
Keyword(s):  
Visible Light ◽  
Triple Bond ◽  
Room Temperature ◽  
Direct Synthesis ◽  
Oxidative Cleavage ◽  
Organic Dye ◽  
Reaction Conditions ◽  
Radical Coupling ◽  
Activated Alkynes ◽  
Key Features

<p>The direct oxidative cleavage of activated alkynes <i>via</i> hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an insitu formed enamines undergo radical coupling with oxidant which finally delivers the oxamates. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as photocatalyst, TBHP plays dual role as “O” source and for the regeneration of photocatalyst. <br></p>

Dual photoredox and nickel-catalyzed desymmetric C–O coupling reactions: visible light-mediated enantioselective synthesis of 1,4-benzodioxanes

2018 ◽  
Vol 5 (21) ◽  
pp. 3098-3102 ◽  
Author(s):  
Quan-Quan Zhou ◽  
Fu-Dong Lu ◽  
Dan Liu ◽  
Liang-Qiu Lu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Coupling Reaction ◽  
Cross Coupling ◽  
Enantioselective Synthesis ◽  
Coupling Reactions ◽  
Nickel Catalysis ◽  
Reaction Conditions ◽  
Cross Coupling Reaction

Chiral 2,2′-bipyridine ligands are key to success in an enantioselective desymmetric C–O cross coupling reaction via dual visible light photoredox and nickel catalysis, resulting in chiral 1,4-benzodioxanes under mild reaction conditions.

scholarly journals Recent advances in visible light-activated radical coupling reactions triggered by (i) ruthenium, (ii) iridium and (iii) organic photoredox agents

2021 ◽  
Author(s):  
Jonathan D. Bell ◽  
John A. Murphy
Keyword(s):  
Visible Light ◽  
Coupling Reactions ◽  
Birch Reduction ◽  
Radical Coupling ◽  
Recent Advances

Visible light-activated reactions continue to expand and diversify. The example shown here is a Birch reduction achieved by organophotoredox reagents.

scholarly journals Visible-Light-Induced Oxidative Cleavage of C-C Triple Bond via Hydroamination: Direct Synthesis of Oxamates from Amines and Activated Alkynes

2018 ◽  
Author(s):  
Sharada Duddu. S ◽  
Sagar Arepally ◽  
Arumugavel Murugan ◽  
Mamata Ojha
Keyword(s):  
Visible Light ◽  
Triple Bond ◽  
Room Temperature ◽  
Direct Synthesis ◽  
Oxidative Cleavage ◽  
Organic Dye ◽  
Reaction Conditions ◽  
Radical Coupling ◽  
Activated Alkynes ◽  
Key Features

<p>The direct oxidative cleavage of activated alkynes <i>via</i> hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an insitu formed enamines undergo radical coupling with oxidant which finally delivers the oxamates. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as photocatalyst, TBHP plays dual role as “O” source and for the regeneration of photocatalyst. <br></p>

scholarly journals Visible-Light-Induced Oxidative Cleavage of C-C Triple Bond via Hydroamination: Direct Synthesis of Oxamates from Amines and Activated Alkynes

2019 ◽  
Author(s):  
Sharada Duddu. S ◽  
Sagar Arepally ◽  
Arumugavel Murugan ◽  
Narenderreddy Katta ◽  
Mamata Ojha
Keyword(s):  
Visible Light ◽  
Triple Bond ◽  
Room Temperature ◽  
Direct Synthesis ◽  
Oxidative Cleavage ◽  
Organic Dye ◽  
Reaction Conditions ◽  
Radical Coupling ◽  
Activated Alkynes ◽  
Key Features

<p>The direct oxidative cleavage of activated alkynes <i>via</i> hydroamination has been described using organic photocatalyst under visible-light irradiation at room temperature. In this reaction, the single electron oxidation of an insitu formed enamines undergo radical coupling with oxidant which finally delivers the oxamates. The key features of this photocatalytic reaction are the mild reaction conditions, metal-free organic dye as photocatalyst, TBHP plays dual role as “O” source and for the regeneration of photocatalyst. <br></p>

Visible light induced radical coupling reactions for the synthesis of conventional polycondensates

2019 ◽  
Vol 10 (41) ◽  
pp. 5652-5658 ◽  
Author(s):  
Busra Nakipoglu ◽  
Gorkem Yilmaz ◽  
Yusuf Yagci
Keyword(s):  
Visible Light ◽  
Synthetic Method ◽  
Coupling Reactions ◽  
Radical Coupling

We herein report a facile visible light induced synthetic method for preparing a series of conventional polycondensates, namely polyesters, polyurethanes and polyamides.

An Unprecedented Cyano-Induced Sodium Nitrite-Catalyzed C(sp3)-H and C(sp2)-H Coupling Reaction

2018 ◽  
Vol 15 (7) ◽  
pp. 989-994 ◽  
Author(s):  
Ling Li ◽  
Bo Su ◽  
Yuxiu Liu ◽  
Qingmin Wang
Keyword(s):  
Sodium Nitrite ◽  
Oxidative Coupling ◽  
High Resolution Mass Spectrometry ◽  
Coupling Reaction ◽  
13C Nmr Spectroscopy ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
1H And 13C Nmr ◽  
Oxidative Coupling Reaction ◽  
Oxidative Coupling Reactions

Aim and Objective: During the investigation of sodium nitrite-catalyzed oxidative coupling reaction of aryls, an unprecedented C(sp2)-H and C(sp3)-H coupling of substituted 2-aryl acetonitrile was found. Materials and Methods: The structure of the coupled product was confirmed by 1H and 13C NMR spectroscopy and high-resolution mass spectrometry (HRMS), and comparison of its derivatives with known compounds. The effects of methoxy group in the benzene ring on the reaction were evaluated. Results: The optimized reaction conditions are summarized as follows: CF3SO3H/substrate = 1.5 equiv., NaNO2/substrate = 0.3 equiv., CH3CN as solvent. 2-(4-Methoxyphenyl)acetonitrile and 2-(3,4,5- trimethoxyphenyl)acetonitrile could also generate C(sp2)-H and C(sp3)-H coupling. The coupling reaction occurred as a typical radial mechanism. Conclusion: An unprecedented cyano-induced, NaNO2-catalyzed oxidative C(sp3)-H and C(sp2)-H coupling was reported. The reaction proceeded under very mild conditions, using O2 in the air as terminal oxidant. The unique oxidative manner might provide more inspiration for the development of intriguing oxidative coupling reactions.

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

scholarly journals Visible Light Photochemical Reactions for Nucleic Acid-Based Technologies

Molecules ◽  
2021 ◽  
Vol 26 (3) ◽  
pp. 556
Author(s):  
Bonwoo Koo ◽  
Haneul Yoo ◽  
Ho Jeong Choi ◽  
Min Kim ◽  
Cheoljae Kim ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Nucleic Acids ◽  
Visible Light ◽  
Chemical Reactions ◽  
Chemical Biology ◽  
Photochemical Reactions ◽  
Reaction Conditions ◽  
Promising Tool ◽  
Recent Developments ◽  
Visible Light Driven

The expanding scope of chemical reactions applied to nucleic acids has diversified the design of nucleic acid-based technologies that are essential to medicinal chemistry and chemical biology. Among chemical reactions, visible light photochemical reaction is considered a promising tool that can be used for the manipulations of nucleic acids owing to its advantages, such as mild reaction conditions and ease of the reaction process. Of late, inspired by the development of visible light-absorbing molecules and photocatalysts, visible light-driven photochemical reactions have been used to conduct various molecular manipulations, such as the cleavage or ligation of nucleic acids and other molecules as well as the synthesis of functional molecules. In this review, we describe the recent developments (from 2010) in visible light photochemical reactions involving nucleic acids and their applications in the design of nucleic acid-based technologies including DNA photocleaving, DNA photoligation, nucleic acid sensors, the release of functional molecules, and DNA-encoded libraries.

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