Literature DB >> 28078753

Photoredox-Catalysed Decarboxylative Alkylation of N-Heteroarenes with N-(Acyloxy)phthalimides.

Wan-Min Cheng1, Rui Shang1,2, Ming-Chen Fu1, Yao Fu1.   

Abstract

An iridium photoredox catalyst in combination with either a stoichiometric amount of Brønsted acid or a catalytic amount of Lewis acid is capable of catalyzing regioselective alkylation of N-heteroarenes with N-(acyloxy)phthalimides at room temperature under irradiation. A broad range of N-heteroarenes can be alkylated using a variety of secondary, tertiary, and quaternary carboxylates. Mechanistic studies suggest that an IrII /IrIII redox catalytic cycle is responsible for the observed reactivity.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  N-(acyloxy)phthalimides; alkylation; decarboxylation; nitrogen heterocycles; photocatalysis

Year:  2017        PMID: 28078753     DOI: 10.1002/chem.201605640

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  14 in total

Review 1.  Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors:  Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal:  Chem Rev       Date:  2021-11-23       Impact factor: 60.622

2.  Advancements in Visible-Light-Enabled Radical C(sp)2-H Alkylation of (Hetero)arenes.

Authors:  Alexandra C Sun; Rory C McAtee; Edward J McClain; Corey R J Stephenson
Journal:  Synthesis (Stuttg)       Date:  2019-01-25       Impact factor: 2.969

3.  Synthesis of Cyclic Anhydrides via Ligand-Enabled C-H Carbonylation of Simple Aliphatic Acids.

Authors:  Zhe Zhuang; Alastair N Herron; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

4.  The photochemical alkylation and reduction of heteroarenes.

Authors:  T McCallum; S P Pitre; M Morin; J C Scaiano; L Barriault
Journal:  Chem Sci       Date:  2017-09-11       Impact factor: 9.825

5.  Diacetyl as a "traceless" visible light photosensitizer in metal-free cross-dehydrogenative coupling reactions.

Authors:  Chia-Yu Huang; Jianbin Li; Wenbo Liu; Chao-Jun Li
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

6.  Photoinitiated Three-Component α-Perfluoroalkyl-β-heteroarylation of Unactivated Alkenes via Electron Catalysis.

Authors:  Danqing Zheng; Armido Studer
Journal:  Org Lett       Date:  2018-12-21       Impact factor: 6.005

7.  Photoredox-catalyzed stereoselective alkylation of enamides with N-hydroxyphthalimide esters via decarboxylative cross-coupling reactions.

Authors:  Jing-Yu Guo; Ze-Yu Zhang; Ting Guan; Lei-Wen Mao; Qian Ban; Kai Zhao; Teck-Peng Loh
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

8.  A Visible Light-Driven Minisci-Type Reaction with N-Hydroxyphthalimide Esters.

Authors:  Lisa Marie Kammer; Aliyaah Rahman; Till Opatz
Journal:  Molecules       Date:  2018-03-27       Impact factor: 4.411

9.  A Fully Automated Continuous-Flow Platform for Fluorescence Quenching Studies and Stern-Volmer Analysis.

Authors:  Koen P L Kuijpers; Cecilia Bottecchia; Dario Cambié; Koen Drummen; Niels J König; Timothy Noël
Journal:  Angew Chem Int Ed Engl       Date:  2018-07-27       Impact factor: 15.336

10.  Site-selective remote C(sp3)-H heteroarylation of amides via organic photoredox catalysis.

Authors:  Hui Chen; Wenjing Fan; Xiang-Ai Yuan; Shouyun Yu
Journal:  Nat Commun       Date:  2019-10-18       Impact factor: 14.919

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