Visible-light-promoted acyl radical cascade reaction for accessing acylated isoquinoline-1,3(2H,4H)-dione derivatives

2020 ◽  
Vol 18 (10) ◽  
pp. 1940-1948 ◽  
Author(s):  
Yingpeng Su ◽  
Rong Zhang ◽  
Wenxuan Xue ◽  
Xuan Liu ◽  
Yanan Zhao ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Acyl Radical ◽  
Keto Acids ◽  
Radical Cascade

A visible-light-promoted radical acylation/cyclization cascade reaction of N-methacryloylbenzamides with α-keto acids was developed to construct acylated isoquinoline-dione derivatives.

Visible-light-mediated radical cascade reaction: synthesis of 3-bromocoumarins from alkynoates

2017 ◽  
Vol 15 (41) ◽  
pp. 8820-8826 ◽  
Author(s):  
Shangbiao Feng ◽  
Jinlai Li ◽  
Zaimin Liu ◽  
Haiyu Sun ◽  
Hongliang Shi ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Radical Addition ◽  
Reaction Synthesis ◽  
Radical Cascade

The development of a visible-light mediated bromo radical addition/spirocyclization/ester migration cascade reaction to generate 3-bromocoumarins from alkynoates is reported.

scholarly journals Asymmetric Total Synthesis of (+)-21-epi-Eburnamonine Via a Photocatalytic Radical Cascade Reaction

2020 ◽  
Author(s):  
Yuan Huang ◽  
Fanglin Xue ◽  
Hengmao Liu ◽  
Fei Xue ◽  
Xiao-Yu Liu ◽  
...  
Keyword(s):  
Total Synthesis ◽  
Visible Light ◽  
Claisen Rearrangement ◽  
Cascade Reaction ◽  
Ring System ◽  
Asymmetric Total Synthesis ◽  
Radical Cascade ◽  
Key Features ◽  
Quaternary Stereocenter ◽  
Visible Light Photocatalytic

Abstract An asymmetric total synthesis of (+)-21-epi-eburnamonine has been achieved. Key features of the synthesis include a visible-light photocatalytic intra-/intramolecular radical cascade reaction to assemble the tetracyclic ABCD ring system, and a highly diastereoselective Johnson-Claisen rearrangement to establish the C20 all-carbon quaternary stereocenter. Graphic Abstract

scholarly journals Radical Carbonylative Synthesis of Heterocycles by Visible Light Photoredox Catalysis

Catalysts ◽  
2020 ◽  
Vol 10 (9) ◽  
pp. 1054
Author(s):  
Xiao-Qiang Hu ◽  
Zi-Kui Liu ◽  
Wen-Jing Xiao
Keyword(s):  
Visible Light ◽  
Efficient Synthesis ◽  
Acyl Radical ◽  
Acyl Chlorides ◽  
Aryl Radicals ◽  
Keto Acids ◽  
Acyl Radicals ◽  
Different Types ◽  
The Impact ◽  
Visible Light Photocatalytic

Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors.

Photoinduced efficient synthesis of cyanoalkylsulfonylated oxindoles via sulfur dioxide insertion

2021 ◽  
Author(s):  
Fan Teng ◽  
Juan Du ◽  
Changping Xun ◽  
Mengxue Zhu ◽  
Ziqin Lu ◽  
...  
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Cascade Reaction ◽  
Efficient Synthesis ◽  
Radical Cascade

A visible-light-promoted radical cascade reaction of N-arylacrylamide and cyclobutanone oxime esters with sulfur dioxide insertion is established.

scholarly journals Synthesis of 3-CF2-Containing Chromones via a Visible-Light-Induced Radical Cascade Reaction of o-Hydroxyaryl Enaminones

ACS Omega ◽  
2017 ◽  
Vol 2 (7) ◽  
pp. 3168-3174 ◽  
Author(s):  
Huang Gao ◽  
Bei Hu ◽  
Wuheng Dong ◽  
Xiaoshuang Gao ◽  
Lili Jiang ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Radical Cascade

Synthesis of 3-sulfonylquinolines by visible-light promoted metal-free cascade cycloaddition involving N-propargylanilines and sodium sulfinates

2020 ◽  
Vol 44 (8) ◽  
pp. 3189-3193 ◽  
Author(s):  
Jing-Mei Yuan ◽  
Jinnan Li ◽  
Heyang Zhou ◽  
Jiali Xu ◽  
Fengting Zhu ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Metal Free ◽  
Radical Cascade

A visible-light promoted radical cascade reaction of N-propargylanilines with sodium sulfinates as sulfonyl radical precursors was developed under metal-free conditions.

Synthesis of cyclohexylidenehydrazine-fused polycyclics via a photocatalytic radical cascade reaction of 2-ethynylaldehyde hydrazones

2017 ◽  
Vol 53 (12) ◽  
pp. 2036-2039 ◽  
Author(s):  
Nengneng Zhou ◽  
Jing Liu ◽  
Zhongfei Yan ◽  
Zhongkai Wu ◽  
Honglin Zhang ◽  
...  
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Polycyclic Compounds ◽  
Radical Cascade

A general and efficient visible-light photoredox-catalyzed cascade annulation of 2-ethynylaldehyde hydrazones with α-bromo-carbonyls for the synthesis of various cyclohexylidenehydrazine-fused polycyclic compounds is described.

scholarly journals Acyl Radical Chemistry via Visible-Light Photoredox Catalysis

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 303-333 ◽  
Author(s):  
Ming-Yu Ngai ◽  
Arghya Banerjee ◽  
Zhen Lei
Keyword(s):  
Visible Light ◽  
Carboxylic Acids ◽  
Easy Access ◽  
Hypervalent Iodine ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Diverse Range ◽  
Acyl Chlorides ◽  
Keto Acids ◽  
Acyl Radicals

Visible-light photoredox catalysis enables easy access to acyl radicals under mild reaction conditions. Reactive acyl radicals, generated from various acyl precursors such as aldehydes, α-keto acids, carboxylic acids, anhydrides, acyl thioesters, acyl chlorides, or acyl silanes, can undergo a diverse range of synthetically useful transformations, which were previously difficult or inaccessible. This review summarizes the recent progress on visible-light-driven acyl radical generation using transition-metal photoredox catalysts, metallaphotocatalysts, hypervalent iodine catalysts or organic photocatalysts.1 Introduction2 The Scope of This Review3 Aldehydes as a Source of Acyl Radicals4 α-Keto Acids as a Source of Acyl Radicals5 Carboxylic Acids as a Source of Acyl Radicals6 Anhydrides as a Source of Acyl Radicals7 Acyl Thioesters as a Source of Acyl Radicals8 Acyl Chlorides as a Source of Acyl Radicals9 Acyl Silanes as a Source of Acyl Radicals10 Conclusions and Future Outlook

Synthesis of functionalized pyrroloindolinesviaa visible-light-induced radical cascade reaction: rapid synthesis of (±)-flustraminol B

2018 ◽  
Vol 54 (54) ◽  
pp. 7443-7446 ◽  
Author(s):  
Kui Wu ◽  
Yuliu Du ◽  
Zheng Wei ◽  
Ting Wang
Keyword(s):  
Visible Light ◽  
Cascade Reaction ◽  
Rapid Synthesis ◽  
Reaction Condition ◽  
Radical Cascade

We report a visible-light-induced synthesis of functionalized pyrroloindolinesviaa radical cascade reaction,highlighting a mild nature of the reaction condition.

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