Literature DB >> 30681765

Nickel-Catalyzed Asymmetric Reductive Diarylation of Vinylarenes.

David Anthony1, Qiao Lin1, Judith Baudet1, Tianning Diao1.   

Abstract

A nickel-catalyzed asymmetric diarylation reaction of vinylarenes enables the preparation of chiral α,α,β-triarylated ethane scaffolds, which exist in a number of biologically active molecules. The use of reducing conditions with aryl bromides as coupling partners obviates the need for stoichiometric organometallic reagents and tolerates a broad range of functional groups. The application of an N-oxyl radical as a ligand to a nickel catalyst represents a novel approach to facilitate nickel-catalyzed cross-coupling reactions.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  alkenes; aryl bromides; asymmetric catalysis; diarylation; nickel

Year:  2019        PMID: 30681765      PMCID: PMC8864584          DOI: 10.1002/anie.201900228

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


  49 in total

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Authors:  R P Alexander; G J Warrellow; M A W Eaton; E C Boyd; J C Head; J R Porter; J A Brown; J T Reuberson; B Hutchinson; P Turner; B Boyce; D Barnes; B Mason; A Cannell; R J Taylor; A Zomaya; A Millican; J Leonard; R Morphy; M Wales; M Perry; R A Allen; N Gozzard; B Hughes; G Higgs
Journal:  Bioorg Med Chem Lett       Date:  2002-06-03       Impact factor: 2.823

2.  Synergistic Bimetallic Ni/Ag and Ni/Cu Catalysis for Regioselective γ,δ-Diarylation of Alkenyl Ketimines: Addressing β-H Elimination by in Situ Generation of Cationic Ni(II) Catalysts.

Authors:  Prakash Basnet; Shekhar Kc; Roshan K Dhungana; Bijay Shrestha; Timothy J Boyle; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2018-11-06       Impact factor: 15.419

3.  Nickel-Catalyzed Asymmetric Reductive Cross-Coupling To Access 1,1-Diarylalkanes.

Authors:  Kelsey E Poremba; Nathaniel T Kadunce; Naoyuki Suzuki; Alan H Cherney; Sarah E Reisman
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

4.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines.

Authors:  Brian P Woods; Manuel Orlandi; Chung-Yang Huang; Matthew S Sigman; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2017-04-13       Impact factor: 15.419

5.  Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes.

Authors:  Andrés García-Domínguez; Zhaodong Li; Cristina Nevado
Journal:  J Am Chem Soc       Date:  2017-05-10       Impact factor: 15.419

6.  Mechanistic Characterization of (Xantphos)Ni(I)-Mediated Alkyl Bromide Activation: Oxidative Addition, Electron Transfer, or Halogen-Atom Abstraction.

Authors:  Justin B Diccianni; Joseph Katigbak; Chunhua Hu; Tianning Diao
Journal:  J Am Chem Soc       Date:  2019-01-17       Impact factor: 15.419

Review 7.  Recent advances in homogeneous nickel catalysis.

Authors:  Sarah Z Tasker; Eric A Standley; Timothy F Jamison
Journal:  Nature       Date:  2014-05-15       Impact factor: 49.962

8.  Ni-Catalyzed Regioselective Alkylarylation of Vinylarenes via C(sp3)-C(sp3)/C(sp3)-C(sp2) Bond Formation and Mechanistic Studies.

Authors:  Shekhar Kc; Roshan K Dhungana; Bijay Shrestha; Surendra Thapa; Namrata Khanal; Prakash Basnet; Robert W Lebrun; Ramesh Giri
Journal:  J Am Chem Soc       Date:  2018-07-30       Impact factor: 15.419

9.  Copper-Catalyzed Radical Relay for Asymmetric Radical Transformations.

Authors:  Fei Wang; Pinhong Chen; Guosheng Liu
Journal:  Acc Chem Res       Date:  2018-09-05       Impact factor: 22.384

10.  A palladium-catalyzed three-component-coupling strategy for the differential vicinal diarylation of terminal 1,3-dienes.

Authors:  Benjamin J Stokes; Longyan Liao; Aline Mendes de Andrade; Qiaofeng Wang; Matthew S Sigman
Journal:  Org Lett       Date:  2014-08-27       Impact factor: 6.005

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  27 in total

1.  Nickel-Catalyzed Enantioselective Reductive Cross-Coupling Reactions.

Authors:  Kelsey E Poremba; Sara E Dibrell; Sarah E Reisman
Journal:  ACS Catal       Date:  2020-06-24       Impact factor: 13.084

2.  Nickel-Catalyzed Dicarbofunctionalization of Alkenes.

Authors:  Xiaoxu Qi; Tianning Diao
Journal:  ACS Catal       Date:  2020-07-02       Impact factor: 13.084

3.  Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives.

Authors:  Shekhar Kc; Roshan K Dhungana; Namrata Khanal; Ramesh Giri
Journal:  Angew Chem Int Ed Engl       Date:  2020-03-19       Impact factor: 15.336

4.  Enantioselective Radical Addition/Cross-Coupling of Organozinc Reagents, Alkyl Iodides, and Alkenyl Boron Reagents.

Authors:  Matteo Chierchia; Peilin Xu; Gabriel J Lovinger; James P Morken
Journal:  Angew Chem Int Ed Engl       Date:  2019-08-28       Impact factor: 15.336

5.  An Expedient Route to 9-arylmethylanthracene Derivatives via Tandem Ni-catalyzed Alkene Dicarbofunctionalization and Acid-promoted Cyclization-aromatization.

Authors:  Doleshwar Niroula; Rishi R Sapkota; Roshan K Dhungana; Bijay Shrestha; Ramesh Giri
Journal:  Isr J Chem       Date:  2020-02-14       Impact factor: 3.333

6.  New Bisoxazoline Ligands Enable Enantioselective Electrocatalytic Cyanofunctionalization of Vinylarenes.

Authors:  Niankai Fu; Lu Song; Jinjian Liu; Yifan Shen; Juno C Siu; Song Lin
Journal:  J Am Chem Soc       Date:  2019-09-09       Impact factor: 15.419

7.  Mechanism of Ni-Catalyzed Reductive 1,2-Dicarbofunctionalization of Alkenes.

Authors:  Qiao Lin; Tianning Diao
Journal:  J Am Chem Soc       Date:  2019-10-28       Impact factor: 15.419

8.  Three-Component Olefin Dicarbofunctionalization Enabled by Nickel/Photoredox Dual Catalysis.

Authors:  Mark W Campbell; Jordan S Compton; Christopher B Kelly; Gary A Molander
Journal:  J Am Chem Soc       Date:  2019-12-13       Impact factor: 15.419

9.  Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations.

Authors:  Shorouk O Badir; Gary A Molander
Journal:  Chem       Date:  2020-06-11       Impact factor: 22.804

10.  Mechanisms of Nickel-Catalyzed Coupling Reactions and Applications in Alkene Functionalization.

Authors:  Justin Diccianni; Qiao Lin; Tianning Diao
Journal:  Acc Chem Res       Date:  2020-04-02       Impact factor: 22.384

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