Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali-Metal Amides under Air

Angewandte Chemie
Eva HeviaJoaquin Gracia-Alvarez

Abstract

A straightforward alkali-metal-mediated protocol for 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, we show that the presence of moisture is key in favouring formation of the target phenethylamines over competing olefin polymerisation 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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