A practical and general amidation method from isocyanates enabled by flow technology

Williams, Jason D. and Kerr, William J. and Leach, Stuart G. and Lindsay, David M. (2018) A practical and general amidation method from isocyanates enabled by flow technology. Angewandte Chemie International Edition, 57 (37). pp. 12126-12130. ISSN 1521-3773 (https://doi.org/10.1002/anie.201807393)

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Abstract

The addition of carbon nucleophiles to isocyanates represents a conceptually flexible and efficient approach to the preparation of amides. This general synthetic strategy has, however, been relatively underutilized, due to narrow substrate tolerance, and the requirement for less favourable reaction conditions. Herein, we disclose a high‐yielding, mass efficient, and scalable method with appreciable functional group tolerance for the formation of amides by reaction of Grignard reagents with isocyanates. Through the application of flow chemistry, and the use of sub‐stoichiometric amounts of CuBr2, this process has been developed to encompass a broad range of substrates, including reactants found to be incompatible with previously published protocols.

ORCID iDs

Williams, Jason D. ORCID logoORCID: https://orcid.org/0000-0002-4742-6848, Kerr, William J. ORCID logoORCID: https://orcid.org/0000-0002-1332-785X, Leach, Stuart G. and Lindsay, David M. ORCID logoORCID: https://orcid.org/0000-0003-4498-5094;
  • Item type:Article
    ID code:64944
    Dates:
    Date
    Event
    10 September 2018
    Published
    18 July 2018
    Published Online
    18 July 2018
    Accepted
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:31 Jul 2018 10:04
    Last modified:11 Nov 2024 12:03
    URI:https://strathprints.strath.ac.uk/id/eprint/64944
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