Literature DB >> 27709775

Nickel- and Photoredox-Catalyzed Cross-Coupling Reactions of Aryl Halides with 4-Alkyl-1,4-dihydropyridines as Formal Nucleophilic Alkylation Reagents.

Kazunari Nakajima1, Sunao Nojima1, Yoshiaki Nishibayashi2.   

Abstract

A combination of nickel and photoredox catalysts promoted novel cross-coupling reactions of aryl halides with 4-alkyl-1,4-dihydropyridines. 4-Alkyl-1,4-dihydropyridines act as formal nucleophilic alkylation reagents through a photoredox-catalyzed carbon-carbon (C-C) bond-cleavage process. The present strategy provides an alternative to classical carbon-centered nucleophiles, such as organometallic reagents.
© 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C cleavage; cross-coupling; dihydropyridines; nickel catalysts; photoredox catalysts

Year:  2016        PMID： 27709775     DOI： 10.1002/anie.201606513

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


  18 in total

1.  Metallaphotoredox-Catalyzed Cross-Electrophile Csp3-Csp3 Coupling of Aliphatic Bromides.

Authors:  Russell T Smith; Xiaheng Zhang; Juan A Rincón; Javier Agejas; Carlos Mateos; Mario Barberis; Susana García-Cerrada; Oscar de Frutos; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2018-12-10       Impact factor: 15.419

2.  Late-Stage C-H Alkylation of Heterocycles and 1,4-Quinones via Oxidative Homolysis of 1,4-Dihydropyridines.

Authors:  Álvaro Gutiérrez-Bonet; Camille Remeur; Jennifer K Matsui; Gary A Molander
Journal:  J Am Chem Soc       Date:  2017-08-23       Impact factor: 15.419

3.  Aminomethylation of Aryl Halides using α-Silylamines Enabled by Ni/Photoredox Dual Catalysis.

Authors:  Camille Remeur; Christopher B Kelly; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-08-16       Impact factor: 13.084

Review 4.  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

5.  Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox-Catalyzed C(sp2)-C(sp3) Cross-Couplings.

Authors:  Mingbin Yuan; Osvaldo Gutierrez
Journal:  Wiley Interdiscip Rev Comput Mol Sci       Date:  2021-09-21

6.  Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation.

Authors:  Shengzong Liang; Tatsuya Kumon; Ricardo A Angnes; Melissa Sanchez; Bo Xu; Gerald B Hammond
Journal:  Org Lett       Date:  2019-05-03       Impact factor: 6.005

Review 7.  Alkyl Carbon-Carbon Bond Formation by Nickel/Photoredox Cross-Coupling.

Authors:  John A Milligan; James P Phelan; Shorouk O Badir; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2019-02-27       Impact factor: 15.336

8.  Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insights.

Authors:  Jennifer K Matsui; Álvaro Gutiérrez-Bonet; Madeline Rotella; Rauful Alam; Osvaldo Gutierrez; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2018-11-07       Impact factor: 15.336

9.  Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors:  Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal:  Angew Chem Int Ed Engl       Date:  2020-06-05       Impact factor: 15.336

10.  1,4-Dihydropyridines as Alkyl Radical Precursors: Introducing the Aldehyde Feedstock to Nickel/Photoredox Dual Catalysis.

Authors:  Álvaro Gutiérrez-Bonet; John C Tellis; Jennifer K Matsui; Brandon A Vara; Gary A Molander
Journal:  ACS Catal       Date:  2016-10-27       Impact factor: 13.084
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