Potassium hexamethyldisilazane (KHMDS), sodium hexamethyldisilazane (NaHMDS), and lithium hexamethyldisilazane (LiHMDS) are strong non-nucleophilic base reagents useful in a wide variety of chemical reactions and transformations.
Fig. 1. Alkali metal hexamethyldisilazanes
Applications include alkylation, arylation, acylation, ring formation, isomerization, rearrangements, aldol condensations, Wittig and Horner-Emmons reactions and polymerization.
Chemists strive for selectivity and specificity in a reaction to increase the yield of the desired product and minimize by-product formation. High selectivity and specificity can lead to simpler, less expensive purification routes to the desired product. Alkali metal hexamethyldisilazane (MHMDS) bases can help achieve these goals. They are selective base reagents due to the following characteristics:
MHMDSs (M=Li, Na, K) can catalyze transition metal-free reactions and act as a ligand while reacting with a wide range of metal halides forming M(HMDS)x catalysts. This topic covers a wide range of applications, please review the individual technical notes for additional information.
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