New two‐step procedures that include an initial regioselective intermolecular hydroaminoalkylation of 2‐allyl‐, 2‐allyldimethylsilyl‐, or 2‐dimethyl(vinyl)silyl‐substituted 3‐bromothiophenes or 3‐bromobenzothiophenes with secondary amines and a subsequent intramolecular Buchwald‐Hartwig amination give direct access to structurally novel bicyclic heterocycles including tetrahydrothienopyridines, tetrahydrothienoazasilines, tetrahydrobenzothienoazasilines, and tetrahydrobenzothienoazasilepines. The hydroaminoalkylation reaction is catalyzed by a mono(aminopyridinato) titanium complex which delivers the branched hydroaminoalkylation products or in the case of vinylsilyl‐substituted substrates, the use of a bis(aminopyridinato) titanium complex gives access to the linear regioisomers. While in the latter case, the hydroaminoalkylation products need to be purified prior to the palladium‐catalyzed amination step, all other two‐step sequences can be run as a one‐pot procedure.