Ambient moisture accelerates hydroamination reactions of vinylarenes with alkali-metal amides under air

Mulks, Florian F. and Bole, Leonie J. and Davin, Laia and Hernán-Gómez, Alberto and Kennedy, Alan and García-Álvarez, Joaquín and Hevia, Eva (2020) Ambient moisture accelerates hydroamination reactions of vinylarenes with alkali-metal amides under air. Angewandte Chemie - International Edition, 59 (43). pp. 19021-19026. ISSN 1521-3773 (https://doi.org/10.1002/anie.202008512)

[thumbnail of Mulks-etal-ACIE-2020-Ambient-moisture-accelerates-hydroamination-reactions-of-vinylarenes-with-alkali-metal-amides-under-air]
Preview
 Text. Filename: Mulks_etal_ACIE_2020_Ambient_moisture_accelerates_hydroamination_reactions_of_vinylarenes_with_alkali_metal_amides_under_air.pdf
Accepted Author Manuscript
Download (736kB)| Preview

Abstract

A straightforward alkali-metal-mediated hydroamination of styrenes using biorenewable 2-methyltetrahydrofuran as a solvent is reported. Refuting the conventional wisdom of the incompatibility of organolithium reagents with air and moisture, shown here is that the presence of moisture is key in favoring formation of the target phenethylamines over competing olefin polymerization products. The method is also compatible with sodium amides, with the latter showing excellent promise as highly efficient catalysts under inert atmosphere conditions.

ORCID iDs

Mulks, Florian F., Bole, Leonie J., Davin, Laia, Hernán-Gómez, Alberto ORCID logoORCID: https://orcid.org/0000-0001-8150-7249, Kennedy, Alan ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, García-Álvarez, Joaquín and Hevia, Eva ORCID logoORCID: https://orcid.org/0000-0002-3998-7506;
  • Item type:Article
    ID code:74379
    Dates:
    Date
    Event
    19 October 2020
    Published
    21 July 2020
    Published Online
    21 July 2020
    Accepted
    Notes:This is the peer reviewed version of the following article: Mulks, F. F., Bole, L. J., Davin, L., Hernán-Gómez, A., Kennedy, A., García-Álvarez, J., & Hevia, E. (2020). Ambient moisture accelerates hydroamination reactions of vinylarenes with alkali-metal amides under air. Angewandte Chemie - International Edition, 59(43), 19021-19026. , which has been published in final form at https://doi.org/10.1002/anie.202008512. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Pure Administrator
    Date deposited:27 Oct 2020 15:24
    Last modified:11 Nov 2024 12:53
    URI:https://strathprints.strath.ac.uk/id/eprint/74379
CORE (COnnecting REpositories)