Synthesis of Quinolines by Visible‐Light Induced Radical Reaction of Vinyl Azides and α‐Carbonyl Benzyl Bromides

Wang, Qile; Huang, Jun; Zhou, Lei

doi:10.1002/adsc.201500141

Cited by 68 publications

(33 citation statements)

References 99 publications

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“…Recently, several groups have described advances in addressing this challenging issue. For instance, acyl oxime and organic azide have been shown as effective iminyl radical precursors under the photoredox catalysis conditions by Leonori, Yu, Zhou, Nevado, Fu, Studer, Pan/Zhou/Han and our group (Scheme a) . Despite these significant achievements, there still remains ample room for the exploitation of such radical species in hydroimination of alkenes in view of the economical and ecological advantages of this strategy.…”

Section: Methodsmentioning

confidence: 99%

Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N,N′‐Dimethylpropylene Urea as H‐Donor

Cai

Wang

et al. 2018

Adv Synth Catal

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Synthesis of 3,4-pyrroline derivatives via visible-light-induced hydro/oxyimination of unactivated olefins is reported. In the presence of the photoredox catalyst fac-Ir(ppy) 3 , the key iminyl radical intermediate can be readily generated from O-acyl oximes, and undergoes intramolecular cyclization and H-abstraction from solvent or is trapped by TEMPO to give the corresponding hydro/oxyimination product, respectively. Mechanistic investigations indicate that N,N'-dimethylpropylene urea (DMPU) works as both reducing agent for catalyst regeneration and H-donor for product formation in this process.

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Section: Methodsmentioning

confidence: 99%

Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N,N′‐Dimethylpropylene Urea as H‐Donor

Cai

Wang

et al. 2018

Adv Synth Catal

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“…In 2015, Lei Zhou and co-workers developed an efficient protocol for the synthesis of Quinolines from vinyl azides with α-carbonyl benzyl bromides via Visible-Light mediated radical reaction. [86] (Scheme 21) The reaction of vinyl azide, 51 and methyl 2-bromo-2-phenylacetate, (as a radical precursor) in the presence of Ir(ppy) 3 catalyst, 18-crown-6 (crown ether), and K 2 HPO 4 base, in acetonitrile/methanol (1 : 1) solution was irradiated under 5 W blue LED for 18 h resulted in desired quinoline 53 product. The reaction undergoes via Visible-light induced intramolecular radical cyclization [85] and deprotonation to provide the corresponding Quinoline in good yields, with broad substrate scope.…”

Section: Visible-light Induced Radical Transformations Towards Quinolmentioning

confidence: 99%

Radical Transformations towards the Synthesis of Quinoline: A Review

Teja

Khan

2020

Chemistry An Asian Journal

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Quinoline is considered one of the most ubiquitous heterocycles due to its engaging biological activities and synthetic utility over organic transformations. Over the past few decades, numerous reports have been documented in the synthesis of quinolines. The classical methods including, Skraup, Friedlander, Doebner‐von‐Miller, Conrad‐Limpach, Pfitzinger quinoline synthesis, and so forth, these are the well‐known methods to construct principal quinoline scaffold with several advantages and limitations. Recently, radical insertion or catalyzed reactions have emerged as a powerful and efficient tool to construct heterocycles with high atom efficiency and step economy. In this concern, this minireview mainly focused on the developments of Quinoline synthesis via radical reactions. In addition, a brief description of the preparation procedure, reactivity, and mechanisms is also included, where as possible. Respectively, the synthesis of quinolines is classified and summarized based on its reactivity, so it will help the researchers to grab the information in this exploration area, as Quinolines are promising pharmacophores.

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“…Light-promoted single-electron transfer from fac-Ir(ppy) 3 to 83 followed by loss of Brgave radicals that subsequently added to vinyl azides 42, affording iminyl radicals that were poised to form quinolines 84 (Scheme 39). 48 A variety of different benzylic bromides were tolerated in the reaction.…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Recent Advances in Iminyl Radical Cyclizations

2017

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Iminyl radical cyclizations have emerged as important tools for constructing five-and six-membered nitrogen-containing heterocycles. Both aromatic and nonaromatic ring systems are readily accessible from a variety of radical precursors. This short review focuses on recently discovered iminyl radical cyclizations. Methods that use heat, transition metals, or oxidants to generate the radicals are discussed, as are protocols employing either UV irradiation or visible light. Many of these newly developed procedures should be quite useful to the organic synthesis community due to their utilization of mild and convenient conditions.

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Synthesis of Quinolines by Visible‐Light Induced Radical Reaction of Vinyl Azides and α‐Carbonyl Benzyl Bromides

Abstract: Avisible-light induced radical reactiono f vinyl azides and a-carbonyl benzyl bromides was developed, which provides an efficient route to polysubstituted quinolines via aC À Ca nd C À N bond formation sequence.

Cited by 68 publications

References 99 publications

Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N,N′‐Dimethylpropylene Urea as H‐Donor

Pyrroline Synthesis via Visible‐Light‐Promoted Hydroimination of Unactivated Alkenes with N,N′‐Dimethylpropylene Urea as H‐Donor

Radical Transformations towards the Synthesis of Quinoline: A Review

Recent Advances in Iminyl Radical Cyclizations

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