Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7‐Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using <i>N</i>‐(Acyloxy)phthalimides as Radical Source

Correia, José Tiago Menezes; Silva, Gustavo Piva da; André, Elias; Paixão, Márcio W.

doi:10.1002/adsc.201900657

Cited by 34 publications

(39 citation statements)

References 70 publications

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“…Recently, in continuation of our investigations on visible light photocatalytic cascade processes, we reported a photoredox radical cascade strategy between NHPI esters and 1,7-enynes. 12 This mild and versatile methodology afforded a family of densely functionalized cyclopenta [c]quinolinones in moderate to good yields. However, no product was detected when tertiary NHPI esters were employed, probably due to the unfavourable 1,5-HAT and very slow 1,6-HAT processes as well as the absence of an external H-donor (Scheme 2a).…”

Section: Introductionmentioning

confidence: 99%

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

et al. 2020

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A metal-and catalyst-free photoinduced radical cascade hydroalkylation of 1,7-enynes has been disclosed. The process is triggered by a SET event involving a photoexcited electron-donoraceptor complex between NHPI ester and Hantzsch ester, which decomposes to afford a tertiary radical that is readily trapped by the enyne. The method provides an operationally simple, robust and stepeconomical approach to the construction of diversely functionalized dihydroquinolinones bearing quaternary-centers. A sequential onepot hydroalkylation-isomerization approach is also allowed giving access to a family of quinolinones. A wide substrate scope and high functional group tolerance was observed in both approaches.

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Section: Introductionmentioning

confidence: 99%

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

et al. 2020

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“…Recently, NHPI esters were investigated in photocatalyzed C−C/C‐heteroatom bond forming reactions for the synthesis of N ‐heterocyclic compounds [41,42,162] . Dihydroquinolinones are important N ‐heterocyclic scaffolds in natural and synthetic products [163] .…”

Section: Photoinduced Radical Cascade Cyclizations Promoted By Eda Complexesmentioning

confidence: 99%

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

et al. 2021

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Photocatalyzed organic synthesis transformation is a remarkable green synthetic strategy because of the advantages of operational simplicity, high chemoselectivities, cheap, and environmental benignancy, along with the extensive applications in the fields of organic, pharmaceutical and functional material chemistry. Generally, photoredox catalysts or photosensitizers are necessary for the generation of their excited states to perform the successive oxidative or reductive reactions through the single electron transfer (SET) or energy transfer (ET) process. Furthermore, the exploration of a colored electron donor-acceptor (EDA) complex or a charge transfer (CT) complex between an electron-rich and an electron-poor substrate provides the chance to deliver the excited intermediate under the irradiation of light, resulting in the formation of radical activate species through a single electron transfer to induce successive various radical reactions. These reactions were performed without the need of any external photocatalysts under mild reaction conditions. Herein, this review focuses on the recent progress on photoinduced radical addition reactions, radical borylations, reductive reactions, radical-radical cross-coupling reactions, degradation reactions and radical cascade cyclization via EDA complexes. We highlight these novel green synthetic methodologies and applications, as well as the mechanisms. This review will help to provide references for organic and medicinal chemists who are charmed by these green organic photochemical transformations based on EDA complexes.

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“…Secondary cyclic and acyclic aliphatic NHPI esters 76 performed satisfactorily. However, the reaction has shown to be not applicable to primary, tertiary, and benzylic NHPI esters [64] …”

Section: Recent Developments On the Photocatalytic Synthesis Of Quinolinone Derivativesmentioning

confidence: 99%

“…However, the reaction has shown to be not applicable to primary, tertiary, and benzylic NHPI esters. [64] Mechanistically, the transformation is initiated by the quenching of the photoexcited iridium photocatalyts (*Ir(III), E red1/2 = À 0.96 V) by the NHPI ester (E red 1/2 < À 1.28 V vs. SCE in MeCN). As mentioned before, the redox potentials mismatch was overcome by hydrogen-bonding interactions between the NHPI ester and water.…”

Section: Recent Developments On the Photocatalytic Synthesis Of Quinolinone Derivativesmentioning

confidence: 99%

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Correia

Santos

Pissinati

et al. 2021

The Chemical Record

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Over the last decade, visible‐light photocatalysis has proved to be a powerful tool for the construction of N‐heterocyclic frameworks, important constituents of natural products, insecticides, pharmacologically relevant therapeutic agents and catalysts. This account highlights recent developments and established methods towards the photocatalytic cascades for preparation of different classes of N‐heterocycles, giving emphasis on our contribution to the field.

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Photoredox Decarboxylative Alkylation/(2+2+1) Cycloaddition of 1,7‐Enynes: A Cascade Approach Towards Polycyclic Heterocycles Using N‐(Acyloxy)phthalimides as Radical Source

Abstract: No Abstract

Cited by 34 publications

References 70 publications

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

Metal-Free Photoinduced Hydroalkylation Cascade Enabled by an Electron-Donor–Acceptor Complex

Progress in Photoinduced Radical Reactions using Electron Donor‐Acceptor Complexes

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

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