Hauser base

Hauser bases, also called magnesium amide bases, are magnesium compounds used in organic chemistry as bases for metalation reactions. These compounds were first described by Charles R. Hauser in 1947.^[1]

Preparation

The Hauser bases are prepared by mixing an amine and a Grignard reagent.

R₂NH + R'MgBr → R₂NMgBr + R'H

Commonly used Hauser bases

iPr₂NMgBr

TMPMgBr (TMP = 2,2,6,6,tetramethylpiperidino)

Uses

Hauser bases are generally used as metalation reagents, like organolithiums or amides. Eaton et al. first showed in 1989 the deprotonation of methyl benzoate and N,N-diethylbenzamide.^[2]

References

1. Hauser, C. R.; Walker, H, G. J. Am. Chem. Soc. 1947, 69, 295
2. Eaton, P. E.; Lee, C. H.; Xiong, Y. J. Am. Chem. Soc. 1989, 111, 8016-8018.