Literature DB >> 29722411

Visible light-promoted alkylation of imines using potassium organotrifluoroborates.

Davis P Plasko1, Christopher J Jordan1, Brittney E Ciesa1, Madison A Merrill1, James M Hanna1.   

Abstract

A mild, redox-neutral, alkylation of imines with potassium alkyltrifluoroborates is described. The reaction proceeds under photoredox conditions at ∼30 °C with primary, secondary, and tertiary alkyltrifluoroborates, leading to alkylation products in moderate to good yield in most cases. Aryl-, vinyl-, and cyclopropyltrifluoroborates failed to react under the reported conditions.

Entities:  

Year:  2018        PMID: 29722411      PMCID: PMC6498442          DOI: 10.1039/c8pp00061a

Source DB:  PubMed          Journal:  Photochem Photobiol Sci        ISSN: 1474-905X            Impact factor:   3.982


  5 in total

1.  Photoredox-Catalyzed Multicomponent Petasis Reaction with Alkyltrifluoroborates.

Authors:  Jun Yi; Shorouk O Badir; Rauful Alam; Gary A Molander
Journal:  Org Lett       Date:  2019-05-30       Impact factor: 6.005

Review 2.  Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

Authors:  Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal:  Chem Sci       Date:  2022-04-18       Impact factor: 9.969

3.  Benzylation of Imines with Activated Boronate Nucleophiles.

Authors:  Michael R Hollerbach; Jacob C Hayes; Timothy J Barker
Journal:  European J Org Chem       Date:  2019-01-21

4.  Excited-state palladium-catalysed reductive alkylation of imines: scope and mechanism.

Authors:  Rajesh Kancherla; Krishnamoorthy Muralirajan; Magnus Rueping
Journal:  Chem Sci       Date:  2022-07-07       Impact factor: 9.969

5.  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

  5 in total

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