Abstract
The synthesis of [9]- and [11]thiahelicenes, as well as the preparation of lower homologues such as [5]-, [6]-, and [7]thiahelicenes is reported. Efficient palladium catalyzed coupling reactions were employed. Triorganoindium derivatives were selectively mono-cross-coupled with N-methyl-3,4-dibromomaleimide followed by Stille coupling with the readily available building block naphthodithiophene. Oxidative photocyclization of the conjugated precursors using visible light was employed to synthesize a series of thia[n]helicenes. This modular synthetic methodology is independent of the length of the helical backbone.
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