Literature DB >> 27265019

Single-Electron Transmetalation: Photoredox/Nickel Dual Catalytic Cross-Coupling of Secondary Alkyl β-Trifluoroboratoketones and -esters with Aryl Bromides.

John C Tellis1, Javad Amani1, Gary A Molander1.   

Abstract

The first cross-coupling of secondary alkyl β-trifluoroboratoketones and -esters has been achieved through application of photoredox/nickel dual catalysis. Although the related β-trifluoroboratoamides have been effectively cross-coupled via Pd-catalysis, the corresponding ketones and esters had proven recalcitrant prior to this report. Reactions occur under mild conditions, and a variety of functional groups and sterically and electronically diverse reaction partners are tolerated.

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Year:  2016        PMID: 27265019     DOI: 10.1021/acs.orglett.6b01357

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  9 in total

1.  Harnessing Alkyl Amines as Electrophiles for Nickel-Catalyzed Cross Couplings via C-N Bond Activation.

Authors:  Corey H Basch; Jennie Liao; Jianyu Xu; Jacob J Piane; Mary P Watson
Journal:  J Am Chem Soc       Date:  2017-04-05       Impact factor: 15.419

Review 2.  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

3.  A one-pot successive cyclization-alkylation strategy for the synthesis of 2,3-disubstituted benzo[b]thiophenes.

Authors:  Christopher Cunningham; Matthew Cloyd; Aimee Phillips; Soha Khan; Katherine Whalen; Tanay Kesharwani
Journal:  Org Biomol Chem       Date:  2021-05-12       Impact factor: 3.876

4.  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

5.  Direct Conversion of Carboxylic Acids to Alkyl Ketones.

Authors:  Javad Amani; Gary A Molander
Journal:  Org Lett       Date:  2017-06-12       Impact factor: 6.005

6.  O-Benzyl Xanthate Esters under Ni/Photoredox Dual Catalysis: Selective Radical Generation and Csp3-Csp2 Cross-Coupling.

Authors:  Brandon A Vara; Niki R Patel; Gary A Molander
Journal:  ACS Catal       Date:  2017-05-09       Impact factor: 13.084

7.  Organocatalyzed, Photoredox Heteroarylation of 2-Trifluoroboratochromanones via C-H Functionalization.

Authors:  Jennifer K Matsui; Gary A Molander
Journal:  Org Lett       Date:  2017-02-03       Impact factor: 6.005

Review 8.  Photoredox-Mediated Routes to Radicals: The Value of Catalytic Radical Generation in Synthetic Methods Development.

Authors:  Jennifer K Matsui; Simon B Lang; Drew R Heitz; Gary A Molander
Journal:  ACS Catal       Date:  2017-03-14       Impact factor: 13.084

9.  Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy.

Authors:  Stefano Crespi; Maurizio Fagnoni
Journal:  Chem Rev       Date:  2020-08-06       Impact factor: 60.622

  9 in total

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