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

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

2019 ◽  
Vol 55 (30) ◽  
pp. 4383-4386 ◽  
Author(s):  
Rui Xu ◽  
Chun Cai

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


2013 ◽  
Vol 9 ◽  
pp. 1977-2001 ◽  
Author(s):  
Jie Hu ◽  
Jiang Wang ◽  
Theresa H Nguyen ◽  
Nan Zheng

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.


2020 ◽  
Vol 22 (2) ◽  
pp. 336-341 ◽  
Author(s):  
Shulei Pan ◽  
Min Jiang ◽  
Jinjin Hu ◽  
Ruigang Xu ◽  
Xiaofei Zeng ◽  
...  

A general and efficient visible-light photoredox-catalyzed decarboxylative radical coupling reaction of N-aryl amino acids with aldehydes or ketones for the synthesis of 1,2-amino alcohols in water at room temperature is described.


2020 ◽  
Vol 44 (37) ◽  
pp. 16031-16035
Author(s):  
Zhaowei Lin ◽  
Maojian Lu ◽  
Boyi Liu ◽  
Jing Gao ◽  
Mingqiang Huang ◽  
...  

An efficient protocol for the construction of 1,5-diketones was realized in the presence of organic fluorophore 4CzIPN, diaryliodonium salt, and visible light irradiation.


2016 ◽  
Vol 6 (2) ◽  
pp. 413-416 ◽  
Author(s):  
Mei-jie Bu ◽  
Guo-ping Lu ◽  
Chun Cai

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


2021 ◽  
Author(s):  
Yanling Shen ◽  
Ning Lei ◽  
Cong Lu ◽  
Dailin Xi ◽  
Xinxin Geng ◽  
...  

Simple, modular assembly of complex fluoroalkyl-containing oxindole derivatives with a broad scope and excellent functional group tolerance under mild conditions (metal- and photocatalyst-free). Benzyl iodides were identified as key intermediates.


RSC Advances ◽  
2015 ◽  
Vol 5 (23) ◽  
pp. 17383-17388 ◽  
Author(s):  
Wei Liu ◽  
Sheng Liu ◽  
Hongqi Xie ◽  
Zhixing Qing ◽  
Jianguo Zeng ◽  
...  

Visible light promoted the oxidation of compounds 1 to amides 2 which were easily transferred to compounds 12.


RSC Advances ◽  
2017 ◽  
Vol 7 (69) ◽  
pp. 43655-43659 ◽  
Author(s):  
Allegra Franchino ◽  
Antonia Rinaldi ◽  
Darren J. Dixon

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.


Synlett ◽  
2020 ◽  
Vol 31 (07) ◽  
pp. 677-682 ◽  
Author(s):  
Bin Sun ◽  
Deyu Li ◽  
Xiaohui Zhuang ◽  
Rui Zhu ◽  
Aertuke Aisha ◽  
...  

A facile protocol for visible-light-induced decarboxylative radical coupling of NHP esters with 8-aminoquinoline amides is reported, affording a highly efficient approach to synthesize a variety of 2-alkylated or 2,4-dialkylated 8-aminoquinoline derivatives. The reaction proceeds smoothly without adding any ligand, and provides the corresponding products containing a wide range of functional groups in moderate to excellent yields. This reaction uses readily available starting materials, and proceeds under mild conditions and with operational simplicity.


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