Synthesis and reactivity of stable trisyl(aminomethylphenyl)silylenoid

A highly thermally stable silylenoid, trisyl(aminomethylphenyl)silylenoid (2) was synthesized from the reaction of dimethylaminomethylphenyllithium with a bromosilylenoid, 1. Silylenoid 2 reacted with electrophiles to give the corresponding products, but did not react with alkyllithiums as a nucleophile.

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► A highly thermally stable trisyl(aminomethylphenyl)silylenoid was synthesized.
► Our result provides a new synthetic strategy for congested organosilicon compounds.
► This is the first example of a stable silylenoid having intramolecular donor atom.