C–H arylation of heterocyclic N oxides through in-situ diazotisation of anilines without added promoters : a green and selective coupling process

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Colleville, Aymeric P. and Horan, Richard A. J. and Olazabal, Sandrine and Tomkinson, Nicholas C. O. (2016) C–H arylation of heterocyclic N oxides through in-situ diazotisation of anilines without added promoters : a green and selective coupling process. Organic Process Research and Development, 20 (7). 1283–1296. ISSN 1083-6160 (https://doi.org/10.1021/acs.oprd.6b00117)

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Abstract

A green and selective method for the generation of bi-aryl compounds through C—H arylation of heterocyclic N-oxides is presented in which the addition of ascorbic acid as a promoter is not required for either the generation of an aryldiazonium species or the subsequent arylation. Reaction conditions were optimized through Multivariate Data Analysis, including Orthogonal Projections to Latent Structures (OPLS) and Design of Experiments (DoE) methodologies resulting in further sustainability improvements, and were then applied to a range of substrates to establish the scope and limitations of the process. The reaction was studied using in-situ infra-red spectroscopy and a mechanism is presented that accounts for the available data from this and previous studies. The reaction was also per-formed on a multigram scale, with calorimetry studies to support further scale-up of this promoter-free transformation.

ORCID iDs

Colleville, Aymeric P., Horan, Richard A. J., Olazabal, Sandrine and Tomkinson, Nicholas C. O. ORCID logoORCID: https://orcid.org/0000-0002-5509-0133;
  • Item type:Article
    ID code:56600
    Dates:
    Date
    Event
    30 May 2016
    Published
    29 May 2016
    Accepted
    Notes:This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:04 Jun 2016 00:09
    Last modified:12 Dec 2024 04:21
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/56600
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