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Synfacts 2013; 9(1): 0093
DOI: 10.1055/s-0032-1317743
DOI: 10.1055/s-0032-1317743
Metal-Mediated Synthesis
Metalation of 2-Phenylethyldimethylamine under Mild Conditions
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
17. Dezember 2012 (online)

Significance
The direct benzylic metalation of 2-phenylethylamine derivatives suffers from β-elimination. The authors found that benzylic metalation of 2-phenylethyldimethylamine can be performed at –78 °C with a mixture of t-BuLi and t-BuOK. The metalated species was found to be stable up to –40°C.
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Comment
Interestingly, the metalation cannot be performed with a mixture of t-BuLi and t-BuOLi. Therefore, the potassium cation seems to be crucial for an efficient conversion. Theoretical and structural studies reveal that potassium is important for the lowering of the barrier of the initial deprotonation, as well as for stabilization of the labile anion.
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