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

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

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 languageEnglish
Pages (from-to)19021-19026
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number43
Early online date21 Jul 2020
DOIs
Publication statusPublished - 19 Oct 2020

Keywords

  • alkali metals
  • hydroamination
  • lithium
  • solvent effects
  • synthetic methods

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