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.

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.

De novo synthesis of benzofurans via trifluoroacetic acid catalyzed cyclization/oxidative aromatization cascade reaction of 2-hydroxy-1,4-diones

2019 ◽  
Vol 17 (32) ◽  
pp. 7547-7551 ◽  
Author(s):  
Qiang Sha ◽  
Haixuan Liu
Keyword(s):  
Trifluoroacetic Acid ◽  
De Novo ◽  
Cascade Reaction ◽  
De Novo Synthesis ◽  
Simple Metal ◽  
Metal Free ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Acid Catalyzed

A simple metal-free cyclization/oxidative aromatization reaction starting from 2-hydroxy-1,4-diones for the de novo synthesis of benzofurans was developed.

Visible light mediated metal-free oxidative aromatization of 1,3,5-trisubstituted pyrazolines

2019 ◽  
Vol 60 (34) ◽  
pp. 150932 ◽  
Author(s):  
Sesuraj Babiola Annes ◽  
Rajamani Rajmohan ◽  
Subburethinam Ramesh ◽  
Pothiappan Vairaprakash
Keyword(s):  
Visible Light ◽  
Metal Free ◽  
Oxidative Aromatization

Practical Synthesis of Functionalized Chromeno[3,4-c]pyridine Derivatives via a CuCl2-Catalyzed Tandem Reaction of the Blaise Reaction Intermediates and 3-Cyanocoumarins

Synlett ◽  
2018 ◽  
Vol 29 (07) ◽  
pp. 959-963
Author(s):  
Jian-Jun Li ◽  
Zhiwei Chen ◽  
Yangyang Fan ◽  
Lei Zheng ◽  
Zhaohai Yang
Keyword(s):  
Michael Addition ◽  
Functional Group ◽  
Tandem Reaction ◽  
Pyridine Derivatives ◽  
Reaction Intermediates ◽  
Reaction Conditions ◽  
Purification Technique ◽  
Aromatization Reaction ◽  
Oxidative Aromatization ◽  
Practical Synthesis

This work discloses a novel and efficient protocol for the construction of functionalized chromeno[3,4-c]pyridine derivatives from the Blaise reaction intermediates and 3-cyanocoumarins through a CuCl2-catalyzed sequential Michael addition/intramolecular cyclization/oxidative aromatization reaction. This new method shows the advantages of mild reaction conditions, easy workup, nonchromatographic purification technique, good functional group tolerance, and moderate to good yields.

Transition-metal-free, visible-light-induced oxidative cross-coupling for constructing β-acetylamino acrylosulfones from sodium sulfinates and enamides

2018 ◽  
Vol 5 (1) ◽  
pp. 92-97 ◽  
Author(s):  
Deli Sun ◽  
Ronghua Zhang
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Rose Bengal ◽  
Cross Coupling ◽  
Metal Free

A visible-light-induced, Rose Bengal catalyzed photoredox process for synthesizing β-acetylamino acrylosulfones has been discovered.

Visible-Light-Induced Arene C(sp2)–H Lactonization Promoted by DDQ and tert-Butyl Nitrite

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 261-266 ◽  
Author(s):  
Yiqing Wang ◽  
Shengpeng Wang ◽  
Bajin Chen ◽  
Meichao Li ◽  
Xinquan Hu ◽  
...  
Keyword(s):  
Visible Light ◽  
Atom Economy ◽  
Reaction Conditions ◽  
Metal Free ◽  
Tert Butyl ◽  
Optimized Conditions ◽  
Visible Light Photocatalytic

A visible-light photocatalytic aerobic oxidative lactonization of arene C(sp2)–H bonds proceeds in the presence of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and tert-butyl nitrite (TBN). Under the optimized conditions, a range of 2-arylbenzoic acids is converted into the corresponding benzocoumarin derivatives in moderate to excellent yields. This method is characterized by its atom economy, mild reaction conditions, the use of a green oxidant and metal-free catalysis.

Visible-Light-Driven Phosphonoalkylation of Alkenes

Synlett ◽  
2021 ◽  
Vol 32 (04) ◽  
pp. 378-382
Author(s):  
Yue-Ming Jiang ◽  
Jie Liu ◽  
Qiang Fu ◽  
Yu-Ming Yu ◽  
Da-Gang Yu
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Functional Group ◽  
Reaction Conditions ◽  
Metal Free ◽  
Alkyl Sulfonates ◽  
Visible Light Driven ◽  
High Yields

AbstractPhosphonylation of alkenes is important for the generation of valuable organophosphines. However, redox-neutral difunctionalization of alkenes with readily available H-P(O) compounds remains underdeveloped. Herein, we report the first visible-light-driven redox-neutral phosphonoalkylation of alkenes. A variety of organophosphorus-containing three-membered carbocyclic scaffolds are synthesized from alkene-bearing alkyl sulfonates with H-P(O) compounds. The transition-metal-free protocol displays good functional group tolerance, broad substrate scope, high yields, and mild reaction conditions.

Metal-free visible light driven synthesis of tetrahydroquinoline derivatives utilizing Rose Bengal

Tetrahedron ◽  
2017 ◽  
Vol 73 (31) ◽  
pp. 4627-4633 ◽  
Author(s):  
Jing-Rui Xin ◽  
Jun-Tao Guo ◽  
Dominic Vigliaturo ◽  
Yan-Hong He ◽  
Zhi Guan
Keyword(s):  
Visible Light ◽  
Rose Bengal ◽  
Metal Free ◽  
Visible Light Driven
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