We investigated the dehydrogenative annulation of silylated 1-indole derivatives with alkynes to synthesize a silole-fused indole. The addition of the generated silylium ion to alkynes was followed by the sila-Friedel-Crafts reaction via silyl migration, realizing regioselective dehydrogenative annulation controlled by the steric bulkiness of a base. The optical properties of the obtained siloloindoles indicated fluorescence of which the intensity depends on the location of the fused silole.
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