Visible-light photoredox catalysis: direct synthesis of fused β-carbolines through an oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors

2015 ◽  
Vol 2 (10) ◽  
pp. 1308-1312 ◽  
Author(s):  
D. Chandrasekhar ◽  
Satheesh Borra ◽  
Jeevak Sopanrao Kapure ◽  
Ghule Shailendra Shivaji ◽  
Gannoju Srinivasulu ◽  
...  
Keyword(s):  
Visible Light ◽  
Direct Synthesis ◽  
Photoredox Catalysis ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Flow Microreactors ◽  
Catalyzed Oxidation

Fused β-carbolines were synthesized via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade in batch and flow microreactors.

scholarly journals Visible-light photoredox catalyzed synthesis of pyrroloisoquinolines via organocatalytic oxidation/[3 + 2] cycloaddition/oxidative aromatization reaction cascade with Rose Bengal

2014 ◽  
Vol 10 ◽  
pp. 1233-1238 ◽  
Author(s):  
Carlos Vila ◽  
Jonathan Lau ◽  
Magnus Rueping
Keyword(s):  
Visible Light ◽  
Rose Bengal ◽  
Isoquinoline Alkaloids ◽  
Reaction Conditions ◽  
Metal Free ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Catalyzed Oxidation

Pyrrolo[2,1-a]isoquinoline alkaloids have been prepared via a visible light photoredox catalyzed oxidation/[3 + 2] cycloaddition/oxidative aromatization cascade using Rose Bengal as an organo-photocatalyst. A variety of pyrroloisoquinolines have been obtained in good yields under mild and metal-free reaction conditions.

Visible-Light Photoredox-Catalyzed Cascade Reaction for the Synthesis of Pyrrolo[2,1-a]isoquinoline-Substituted Phosphonates

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 522-529 ◽  
Author(s):  
Deqing Shi ◽  
Lingna Wang ◽  
Tiancong Ma ◽  
Mingming Qiao ◽  
Qiangxian Wu ◽  
...  
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Room Temperature ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
One Pot ◽  
Oxidative Aromatization ◽  
Activated Olefins ◽  
Catalyzed Oxidation

A visible-light photoredox-catalyzed oxidation/[3+2] cycloaddition/oxidative aromatization cascade reaction of [(3,4-dihydroisoquinolin-2(1H)-yl)methyl]phosphonates and activated olefins or alkynes for the efficient synthesis of potentially biological active pyrrolo[2,1-a]isoquinoline-substituted phosphonates was developed. This transformation features mild reaction conditions (i.e., visible light irradiation, room temperature), molecular oxygen (O2) as a green oxidant, simple ‘one-pot’ operation.

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.

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

Synlett ◽  
2021 ◽  
Author(s):  
Ao Li ◽  
Bin Pan ◽  
Mu Chao ◽  
Na Wang ◽  
Yu-Long Li ◽  
...  
Keyword(s):  
Visible Light ◽  
Room Temperature ◽  
Air Atmosphere ◽  
Wide Range ◽  
Convenient Route ◽  
Catalyzed Oxidation

A visible-light-induced direct α-oxygenation of N-substituted tetrahydroisoquinoline derivatives has been successfully developed. Metalloporphyrin (ZnTPP) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to afford the desired products in moderate to good yields at room temperature under air atmosphere.

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

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