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 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.

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 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.

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

Intermolecular Aminotrifluoromethylation of Alkenes by Visible-Light-Driven Photoredox Catalysis

2013 ◽  
Vol 15 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Yusuke Yasu ◽  
Takashi Koike ◽  
Munetaka Akita
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Visible Light Driven

Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis

RSC Advances ◽  
2015 ◽  
Vol 5 (56) ◽  
pp. 44928-44932 ◽  
Author(s):  
Milan Dinda ◽  
Chandan Bose ◽  
Tridev Ghosh ◽  
Soumitra Maity
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Dehydrogenative Coupling

A visible light mediated cross-dehydrogenative-coupling (CDC) reaction has been developed for the synthesis of N-hydroxyester derivatives from aldehydes and N-hydroxyimides.

Visible-Light-Induced Photoredox Catalysis with a Tetracerium-Containing Silicotungstate

2014 ◽  
Vol 53 (21) ◽  
pp. 5356-5360 ◽  
Author(s):  
Kosuke Suzuki ◽  
Fei Tang ◽  
Yuji Kikukawa ◽  
Kazuya Yamaguchi ◽  
Noritaka Mizuno
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis
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