Copper-catalysed C-H functionalisation gives access to 2-aminobenzimidazoles

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Clark, Peter R. and Williams, Glynn D. and Tomkinson, Nicholas C. O. (2019) Copper-catalysed C-H functionalisation gives access to 2-aminobenzimidazoles. Organic and Biomolecular Chemistry, 17 (34). pp. 7943-7955. ISSN 1477-0520 (https://doi.org/10.1039/C9OB01651A)

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Abstract

This paper describes the development, optimisation and exemplification of a copper-catalysed C–H functionalisation to form pharmaceutically relevant 2-aminobenzimidazoles from aryl-guanidines. High throughput screening was used as a tool to identify a catalytically active copper source, DoE was used for reaction optimisation and a range of aryl-guanidines were prepared and exposed to the optimum conditions to afford a range of 2-aminobenzimidazoles in moderate to good yields. The methodology has been applied to the synthesis of Emedastine, a marketed anti-histamine pharmaceutical compound, with the key cyclisation step performed on a gram-scale.

ORCID iDs

Clark, Peter R., Williams, Glynn D. and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
  • Item type:Article
    ID code:71894
    Dates:
    Date
    Event
    14 September 2019
    Published
    13 August 2019
    Published Online
    12 August 2019
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:26 Mar 2020 11:33
    Last modified:11 Nov 2024 12:29
    URI:https://strathprints.strath.ac.uk/id/eprint/71894
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