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Regiocontrolled synthesis of polysubstituted benzenes from silylated 1,3-dien-5-ynes has been achieved by using diisobutylaluminum hydride (DIBAL-H). Hydroalumination of the alkyne moiety with DIBAL-H triggers the aromatic cyclization, which usually proceeds without rearrangement and loss of the existing substituents. The related unusual cyclizations to different types of polysubstituted benzenes are also described.

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Hydroalumination-Triggered Cyclization of Silylated 1,3-Dien-5-ynes to Polysubstituted Benzenes. -In the case of 4-tert-butyl-1,3-Dien-5-yne (IX) a dephenylative aromatization towards (X) is observed. -(KINOSHITA, H.; TOHJIMA, T.; MIURA*, K.; Org. Lett. 16 (2014) 18, 4762-4765, http://dx.