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

Florian F. Mulks; Leonie J. Bole; Laia Davin; Alberto Hernán-Gómez; Alan Kennedy; Joaquín García-Álvarez; Eva Hevia

doi:10.1002/anie.202008512

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

Florian F. Mulks, Leonie J. Bole, Laia Davin, Alberto Hernán-Gómez, Alan Kennedy, Joaquín García-Álvarez, Eva Hevia^*

^*Corresponding author for this work

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

32 Citations (Scopus)

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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.

Original language	English
Pages (from-to)	19021-19026
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	43
Early online date	21 Jul 2020
DOIs	https://doi.org/10.1002/anie.202008512
Publication status	Published - 19 Oct 2020

Funding

We thank Robert Mulvey and Marina Uzelac for useful comments. Funding by the UK's Engineering and Physical Sciences Research Council (Grant number EP/S020837/1), ERC‐Stg MixMetApps, and the University of Bern is also acknowledged.

Keywords

alkali metals
hydroamination
lithium
solvent effects
synthetic methods

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Mulks-etal-ACIE-2020-Ambient-moisture-accelerates-hydroamination-reactions-of-vinylarenes-with-alkali-metal-amides-under-airAccepted author manuscript, 720 KB

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title = "Ambient moisture accelerates hydroamination reactions of vinylarenes with alkali-metal amides under air",

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.",

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AU - Mulks, Florian F.

AU - Bole, Leonie J.

AU - Davin, Laia

AU - Hernán-Gómez, Alberto

AU - Kennedy, Alan

AU - García-Álvarez, Joaquín

AU - Hevia, Eva

N1 - 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.

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Y1 - 2020/10/19

N2 - 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.

AB - 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.

KW - alkali metals

KW - hydroamination

KW - lithium

KW - solvent effects

KW - synthetic methods

U2 - 10.1002/anie.202008512

DO - 10.1002/anie.202008512

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JF - Angewandte Chemie - International Edition

IS - 43

ER -

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

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