Literature DB >> 32633062

Selective 1,2-Aryl-Aminoalkylation of Alkenes Enabled by Metallaphotoredox Catalysis.

Songlin Zheng1, Zimin Chen1, Yuanyuan Hu1, Xiaoxiang Xi1, Zixuan Liao1, Weirong Li1, Weiming Yuan1.   

Abstract

A highly chemo- and regioselective intermolecular 1,2-aryl-aminoalkylation of alkenes by photoredox/nickel dual catalysis is described here. This three-component conjunctive cross-coupling is highlighted by its first application of primary alkyl radicals, which were not compatible in previous reports. The readily prepared α-silyl amines could be transferred to α-amino radicals by photo-induced single electron transfer step. The radical addition/cross-coupling cascade reaction proceeds under mild, base-free and redox-neutral conditions with good functional group tolerance, and importantly, provides an efficient and concise method for the synthesis of structurally valuable α-aryl substituted γ-amino acid derivatives motifs.
© 2020 Wiley-VCH GmbH.

Entities:  

Keywords:  1,2-dicarbofunctionalization; alkenes; conjunctive cross-coupling; metallaphotoredox catalysis; three-component reactions

Year:  2020        PMID: 32633062     DOI: 10.1002/anie.202006439

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


  7 in total

1.  Ni-Catalyzed Arylbenzylation of Alkenylarenes: Kinetic Studies Reveal Autocatalysis by ZnX2 *.

Authors:  Roshan K Dhungana; Rishi R Sapkota; Laura M Wickham; Doleshwar Niroula; Bijay Shrestha; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-09-15       Impact factor: 16.823

2.  Photochemical C-H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.

Authors:  Mark W Campbell; Mingbin Yuan; Viktor C Polites; Osvaldo Gutierrez; Gary A Molander
Journal:  J Am Chem Soc       Date:  2021-03-04       Impact factor: 15.419

3.  The Merger of Benzophenone HAT Photocatalysis and Silyl Radical-Induced XAT Enables Both Nickel-Catalyzed Cross-Electrophile Coupling and 1,2-Dicarbofunctionalization of Olefins.

Authors:  Alberto Luridiana; Daniele Mazzarella; Luca Capaldo; Juan A Rincón; Pablo García-Losada; Carlos Mateos; Michael O Frederick; Manuel Nuño; Wybren Jan Buma; Timothy Noël
Journal:  ACS Catal       Date:  2022-09-01       Impact factor: 13.700

4.  Formal β-C-H Arylation of Aldehydes and Ketones by Cooperative Nickel and Photoredox Catalysis.

Authors:  Kun Liu; Armido Studer
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-23       Impact factor: 16.823

5.  Dual Nickel/Photoredox-Catalyzed Site-Selective Cross-Coupling of 1,2-Bis-Boronic Esters Enabled by 1,2-Boron Shifts.

Authors:  Hui Wang; Wangyujing Han; Adam Noble; Varinder K Aggarwal
Journal:  Angew Chem Int Ed Engl       Date:  2022-07-14       Impact factor: 16.823

6.  General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.

Authors:  Lei Guo; Mingbin Yuan; Yanyan Zhang; Fang Wang; Shengqing Zhu; Osvaldo Gutierrez; Lingling Chu
Journal:  J Am Chem Soc       Date:  2020-11-19       Impact factor: 15.419

7.  Nickel-Catalyzed Regioselective Alkenylarylation of γ,δ-Alkenyl Ketones via Carbonyl Coordination.

Authors:  Roshan K Dhungana; Vivek Aryal; Doleshwar Niroula; Rishi R Sapkota; Margaret G Lakomy; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2021-07-20       Impact factor: 16.823

  7 in total

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