One of the main challenges of current organic synthesis is the design of practically simple and increasingly efficient organic transformations. The sequential formation of various bonds through tandem or cascade reactions constitutes one approach to achieving this goal. In these types of reactions, high molecular complexity can be built from relatively simple starting materials in a single synthetic operation.[1] Moreover, among the advantages of these processes are atom, solvent, and catalyst economy and operational simplicity, as isolation of intermediates is avoided.In the context of transition-metal-catalyzed reactions, processes in which a single, multifunctional metal catalyst promotes various individual reactions (auto-tandem catalysis) [2] are of great interest. By taking advantage of the wide scope, high performance, and remarkable stability of state-ofthe-art Pd catalysts, a variety of Pd-catalyzed processes have been developed based on this principle. [3] We have recently discovered a new Pd-catalyzed C À C bond-forming reaction that employs N-tosylhydrazones as nucleophilic component in a new type of "stoichiometric organometallic-free" cross-coupling process.[4] Moreover, the tosylhydrazone can be generated in situ from a carbonyl compound and tosylhydrazide, which implies that the carbonyl compounds can be directly employed in the crosscoupling reaction (Scheme 1). [5] Following our interest in auto-tandem Pd-catalyzed processes, [3b,c] we decided to investigate whether the new CÀ C bond-forming reaction with tosylhydrazones could be one of the processes promoted by a multifunctional catalyst. Following this idea, we designed a possible sequence employing hydrazones derived from b-aminoketones I and odihalobenzene derivatives II as starting materials. Thus, in the presence of the Pd catalyst two consecutive processes might occur: a CÀC cross-coupling reaction (arylation) to give intermediate III, followed by an intramolecular CÀN bondforming reaction (amination) [6] affording substituted tetrahydroquinolines IV (Scheme 2). Moreover, taking into account that a variety of b-aminoketones are accessible in enantiomerically pure form through asymmetric organocatalyzed Mannich reactions, [7] our ultimate goal would be to develop a heterocyclization process that would preserve the configurationally unstable stereogenic center in the a position to the carbonyl group. [8] We started our study with the model reaction between the hydrazone 2 a, derived from aminoketone 1 a, and 1-bromo-2-chlorobenzene (3 a, Scheme 3). The initial experiments were conducted under standard conditions for the arylation reaction, but in the presence of an excess of base to also promote the intramolecular amination, which gave rise to promising results. The desired tetrahydrophenanthridine 4 a was formed together with significant amounts of cyclohexene 5, which was generated by uncatalyzed thermal degradation of the hydrazone, and arylated cyclohexene 6, which was formed by dehalogenation of the intermediate arylated product.These...