scholarly journals The chemistry of amine radical cations produced by visible light photoredox catalysis

2013 ◽  
Vol 9 ◽  
pp. 1977-2001 ◽  
Author(s):  
Jie Hu ◽  
Jiang Wang ◽  
Theresa H Nguyen ◽  
Nan Zheng
Keyword(s):  
Visible Light ◽  
Radical Cations ◽  
Reactive Intermediates ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Iminium Ions ◽  
Distonic Ions ◽  
Synthetic Intermediates

Amine radical cations are highly useful reactive intermediates in amine synthesis. They have displayed several modes of reactivity leading to some highly sought-after synthetic intermediates including iminium ions, α-amino radicals, and distonic ions. One appealing method to access amine radical cations is through one-electron oxidation of the corresponding amines under visible light photoredox conditions. This approach and subsequent chemistries are emerging as a powerful tool in amine synthesis. This article reviews synthetic applications of amine radical cations produced by visible light photocatalysis.

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

Aroyl chlorides as novel acyl radical precursors via visible-light photoredox catalysis

2017 ◽  
Vol 4 (7) ◽  
pp. 1331-1335 ◽  
Author(s):  
Shi-Ming Xu ◽  
Jian-Qiang Chen ◽  
Dan Liu ◽  
Yun Bao ◽  
Yong-Min Liang ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
First Time

Abundant and inexpensive aroyl chlorides have been employed for the first time as novel acyl radical precursors in visible-light photocatalysis.

Visible light photocatalysis in synthesis of pharmaceutically relevant heterocyclic scaffolds

2022 ◽  
Author(s):  
Vishal Srivastava ◽  
Pravin Kumar Singh ◽  
Shraddha Tivari ◽  
Praveen Pratap Singh
Keyword(s):  
Natural Products ◽  
Visible Light ◽  
Chemical Bond ◽  
Organic Synthesis ◽  
Bond Formation ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Chemical Bond Formation

Visible light and photoredox catalysis have emerged as a powerful and long-lasting tool for organic synthesis, demonstrating the importance of a variety of chemical bond formation methods. Natural products, physiologically...

Excited radical anions and excited anions in visible light photoredox catalysis

2019 ◽  
Vol 4 (12) ◽  
Author(s):  
Indrajit Ghosh
Keyword(s):  
Visible Light ◽  
Organic Synthesis ◽  
Transition Metal Complexes ◽  
Organic Dyes ◽  
Visible Light Photocatalysis ◽  
Radical Anions ◽  
Photoredox Catalysis ◽  
Inorganic Semiconductors ◽  
Redox Active ◽  
Excited Radical

Abstract Over the last decade, visible light photocatalysis has dramatically increased the arsenal of methods for organic synthesis and changed the way we activate molecules for chemical reactions. Polypyridyl transition metal complexes, redox-active organic dyes, and inorganic semiconductors are typically used as photocatalysts for such transformations. This chapter reviews the applications of radical anions and anions as photosensitizers in visible light photoredox catalysis.

scholarly journals Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process

2021 ◽  
Author(s):  
Eloïse Colson ◽  
Julie Andrez ◽  
Ali Dabbous ◽  
Frabrice Dénès ◽  
Vincent Maurel ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Radical Cations ◽  
Photoredox Catalysis ◽  
Radical Intermediates ◽  
Transfer Processes ◽  
Radical Acceptor ◽  
Simple Protocol ◽  
Related Alkaloid ◽  
Electron Transfer Processes

A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials using visible-light photoredox catalysis. This unprecedented annulation process takes advantage of the unique reactivity of ethyl 2-(acetoxymethyl)acrylate as a 1,3-bis radical acceptor and of cyclic N,N-dialkylanilines as radical 1,3-bis radical donors. The success of this process relies on efficient electron transfer processes and highly selective deprotonation of aminium radical cations leading to the key α-amino radical intermediates.

scholarly journals Cascade cyclization reactions of alkylidenecyclopropanes for the construction of polycyclic lactams and lactones by visible light photoredox catalysis

2020 ◽  
Vol 7 (2) ◽  
pp. 374-379 ◽  
Author(s):  
Mintao Chen ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Visible Light ◽  
Membered Ring ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Cyclization Reactions ◽  
Cascade Cyclization

A facile method for the synthesis of seven- and eight-membered ring-containing polycyclic lactams and lactones by visible light photocatalysis has been developed.

ChemInform Abstract: The Chemistry of Amine Radical Cations Produced by Visible Light Photoredox Catalysis

ChemInform ◽  
2014 ◽  
Vol 45 (5) ◽  
pp. no-no
Author(s):  
Jie Hu ◽  
Jiang Wang ◽  
Theresa H. Nguyen ◽  
Nan Zheng
Keyword(s):  
Visible Light ◽  
Radical Cations ◽  
Photoredox Catalysis

scholarly journals Tropane and Related Alkaloid Skeletons via a Radical [3+3]-Annulation Process

2021 ◽  
Author(s):  
Eloïse Colson ◽  
Julie Andrez ◽  
Ali Dabbous ◽  
Frabrice Dénès ◽  
Vincent Maurel ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Radical Cations ◽  
Photoredox Catalysis ◽  
Radical Intermediates ◽  
Transfer Processes ◽  
Radical Acceptor ◽  
Simple Protocol ◽  
Related Alkaloid ◽  
Electron Transfer Processes

A mild and simple protocol for the synthesis of 8-azabicyclo[3.2.1]octane and 9-azabicyclo[3.3.1]nonane derivatives is described. It provides these valuable bicyclic alkaloid skeletons in good yields and high levels of diastereoselectivity from simple and readily available starting materials using visible-light photoredox catalysis. This unprecedented annulation process takes advantage of the unique reactivity of ethyl 2-(acetoxymethyl)acrylate as a 1,3-bis radical acceptor and of cyclic N,N-dialkylanilines as radical 1,3-bis radical donors. The success of this process relies on efficient electron transfer processes and highly selective deprotonation of aminium radical cations leading to the key α-amino radical intermediates.

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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