The first N-heterocyclic carbene (NHC) stabilized silyl-substituted chlorosilylene (1) was isolated via selective dehydrochlorination by NHC from silyl-based Si(IV) precursor tBu3SiSiHCl2. Compound 1 can form an iron chlorosilylene complex (2) with an iron carbonyl dimer and undergoes chloride/hydride metathesis to yield a stable NHC-silylene hydride borane adduct (3). Upon treatment with additional NHC, chlorosilylene 1 was converted into silyl-substituted silyliumylidene ions (4).