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Ambient Moisture Accelerates Hydroamination Reactions of Vinylarenes with Alkali‐Metal Amides under Air
Author(s) -
Mulks Florian F.,
Bole Leonie J.,
Davin Laia,
HernánGómez Alberto,
Kennedy Alan,
GarcíaÁlvarez Joaquín,
Hevia Eva
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202008512
Subject(s) - hydroamination , alkali metal , chemistry , moisture , solvent , olefin fiber , inert gas , reagent , catalysis , inert , polymerization , organic chemistry , metal , polymer chemistry , polymer
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.