Exploiting deep eutectic solvents and organolithium reagent partnerships : chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions

Vidal, Cristian and García-Álvarez, Joaquín and Hernán-Gómez, Alberto and Kennedy, Alan R. and Hevia, Eva (2016) Exploiting deep eutectic solvents and organolithium reagent partnerships : chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions. Angewandte Chemie International Edition, 55 (52). pp. 16145-16148. ISSN 1521-3773 (https://doi.org/10.1002/anie.201609929)

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Abstract

Shattering the long-held dogma that organolithium chemistry needs to be performed under inert atmospheres in toxic organic solvents, chemoselective addition of organolithium reagents to non-activated imines and quinolines has been accomplished in green, biorenewable deep eutectic solvents (DESs) at room temperature and in the presence of air, establishing a novel and sustainable access to amines. Improving on existing methods, this approach proceeds in the absence of additives; occurs without competitive enolization, reduction or coupling processes; and reactions were completed in seconds. Comparing RLi reactivities in DESs with those observed in pure glycerol or THF suggests a kinetic anionic activation of the alkylating reagents occurs, favoring nucleophilic addition over competitive hydrolysis.

ORCID iDs

Vidal, Cristian, García-Álvarez, Joaquín, Hernán-Gómez, Alberto ORCID logoORCID: https://orcid.org/0000-0001-8150-7249, Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015 and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
  • Item type:Article
    ID code:58891
    Dates:
    Date
    Event
    23 December 2016
    Published
    28 November 2016
    Published Online
    3 November 2016
    Accepted
    Notes:This is the peer reviewed version of the following article: Vidal, C., García-Álvarez, J., Hernán-Gómez, A., Kennedy, A. R., & Hevia, E. (2016). Exploiting deep eutectic solvents and organolithium reagent partnerships: chemoselective ultrafast addition to imines and quinolines under aerobic ambient temperature conditions. Angewandte Chemie International Edition, which has been published in final form at https://dx.doi.org/10.1002/anie.201609929. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:30 Nov 2016 10:37
    Last modified:11 Nov 2024 11:34
    Related URLs:
    URI:https://strathprints.strath.ac.uk/id/eprint/58891
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