Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 43, Pages 19021-19026Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202008512
Keywords
alkali metals; hydroamination; lithium; solvent effects; synthetic methods
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Funding
- UK's Engineering and Physical Sciences Research Council [EP/S020837/1]
- ERC-Stg MixMetApps
- University of Bern
- EPSRC [EP/S020837/1] Funding Source: UKRI
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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.
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