silylamides

A silylamide is a chemical compound containing a silicon-nitrogen bond where the nitrogen atom is bonded to at least one silicon atom and at least one organic group, and the silicon atom is bonded to at least one nitrogen atom and at least one organic or inorganic group. The general formula can be represented as R3Si-NR'R'', where R, R', and R'' represent organic or inorganic substituents. If there are multiple silicon atoms attached to a single nitrogen, it can be described as a polysilylamide.

These compounds are often used as reagents in organic synthesis. For instance, lithium bis(trimethylsilyl)amide, often abbreviated as LiHMDS, is a strong, non-nucleophilic base widely employed for deprotonation reactions, particularly in the formation of enolates. Its steric bulk prevents it from acting as a nucleophile, making it selective for proton abstraction. Other silylamides, such as silylated amines, can serve as protecting groups for amine functionalities during complex synthetic sequences. The silicon-nitrogen bond can be cleaved under specific conditions, regenerating the free amine. The reactivity and stability of silylamides are influenced by the nature of the substituents on both the silicon and nitrogen atoms.