Literature DB >> 24729379

Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions.

Jun Xuan1, Xu-Dong Xia, Ting-Ting Zeng, Zhu-Jia Feng, Jia-Rong Chen, Liang-Qiu Lu, Wen-Jing Xiao.   

Abstract

A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  cycloaddition; dyes; heterocycles; photochemistry; synthetic methods

Mesh:

Substances:

Year:  2014        PMID: 24729379     DOI: 10.1002/anie.201400602

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  13 in total

1.  Diverse Reactivity of Diazatitanacyclohexenes: Coupling Reactions of 2H-Azirines Mediated by Titanium(II).

Authors:  Addison N Desnoyer; Xin Yi See; Ian A Tonks
Journal:  Organometallics       Date:  2018-09-10       Impact factor: 3.876

2.  Photoredox-Mediated Net-Neutral Radical/Polar Crossover Reactions.

Authors:  Rebecca J Wiles; Gary A Molander
Journal:  Isr J Chem       Date:  2020-02-18       Impact factor: 3.333

3.  Construction of Polycyclic γ-Lactams and Related Heterocycles via Electron Catalysis.

Authors:  Jun Xuan; Constantin G Daniliuc; Armido Studer
Journal:  Org Lett       Date:  2016-11-29       Impact factor: 6.005

4.  Visible light C-H amidation of heteroarenes with benzoyl azides.

Authors:  E Brachet; T Ghosh; I Ghosh; B König
Journal:  Chem Sci       Date:  2014-10-30       Impact factor: 9.825

Review 5.  Photocatalysis with organic dyes: facile access to reactive intermediates for synthesis.

Authors:  Stephanie G E Amos; Marion Garreau; Luca Buzzetti; Jerome Waser
Journal:  Beilstein J Org Chem       Date:  2020-05-29       Impact factor: 2.883

Review 6.  Green Protocols in Heterocycle Syntheses via 1,3-Dipolar Cycloadditions.

Authors:  Katia Martina; Silvia Tagliapietra; Valery V Veselov; Giancarlo Cravotto
Journal:  Front Chem       Date:  2019-02-26       Impact factor: 5.221

7.  Divergent synthesis of chiral cyclic azides via asymmetric cycloaddition reactions of vinyl azides.

Authors:  Nuligonda Thirupathi; Fang Wei; Chen-Ho Tung; Zhenghu Xu
Journal:  Nat Commun       Date:  2019-07-18       Impact factor: 14.919

8.  Radical-based functionalization-oriented construction: rapid assembly of azaarene-substituted highly functionalized pyrroles.

Authors:  Weigao Hu; Qiangqiang Zhan; Hongwei Zhou; Shanshan Cao; Zhiyong Jiang
Journal:  Chem Sci       Date:  2021-03-29       Impact factor: 9.825

9.  Synthesis of (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine enabled by photoredox catalysis in flow.

Authors:  Joel W Beatty; Corey R J Stephenson
Journal:  J Am Chem Soc       Date:  2014-07-09       Impact factor: 15.419

10.  Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.

Authors:  Xiao-Qiang Hu; Xiaotian Qi; Jia-Rong Chen; Quan-Qing Zhao; Qiang Wei; Yu Lan; Wen-Jing Xiao
Journal:  Nat Commun       Date:  2016-04-06       Impact factor: 14.919

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