A scalable metal-, azide-, and halogen-free method for the preparation of triazoles

Clark, Peter R. and Williams, Glynn D. and Hayes, Jerome F. and Tomkinson, Nicholas C. O. (2020) A scalable metal-, azide-, and halogen-free method for the preparation of triazoles. Angewandte Chemie International Edition, 59 (17). pp. 6740-6744. ISSN 1521-3773 (https://doi.org/10.1002/anie.201915944)

[thumbnail of Clark-etal-ACIE-2020-A-scalable-metal-azide-and-halogen-free-method-for-the-preparation-of-triazoles]
Preview
 Text. Filename: Clark_etal_ACIE_2020_A_scalable_metal_azide_and_halogen_free_method_for_the_preparation_of_triazoles.pdf
Accepted Author Manuscript
Download (798kB)| Preview

Abstract

A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.

ORCID iDs

Clark, Peter R., Williams, Glynn D., Hayes, Jerome F. and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
  • Item type:Article
    ID code:71811
    Dates:
    Date
    Event
    20 April 2020
    Published
    15 January 2020
    Published Online
    15 January 2020
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:19 Mar 2020 12:10
    Last modified:11 Nov 2024 12:34
    URI:https://strathprints.strath.ac.uk/id/eprint/71811
CORE (COnnecting REpositories)