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 1433-7851 (https://doi.org/10.1002/anie.202008512)

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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.

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;