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

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 favor...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie Vol. 132; no. 43; pp. 19183 - 19188
Main Authors Mulks, Florian F., Bole, Leonie J., Davin, Laia, Hernán‐Gómez, Alberto, Kennedy, Alan, García‐Álvarez, Joaquín, Hevia, Eva
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 19.10.2020
Subjects
Alkali metals
Amides
Catalysts
Chemistry
hydroamination
Incompatibility
Inert atmospheres
lithium
Moisture
Reagents
solvent effects
Styrenes
synthetic methods
Online AccessGet full text

Cover

More Information
Summary: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. The nemesis of organo‐alkali‐metal reagents, that is, ambient moisture, can remarkably accelerate the alkali‐metal amide induced hydroamination of styrenes. A practically simple aerobic procedure for these hydroaminations under air and in renewable 2‐methyltetrahydrofuran is revealed.
Bibliography:These authors contributed equally to this work.
In memory of Professor Killian Muñiz
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202008512