Collect. Czech. Chem. Commun. 2000, 65, 577-609

Synthesis of Aromatic Triynes as Precursors to Helicene Derivatives

Irena G. Stará*, Adrian Kollárovič, Filip Teplý, Ivo Starý*, David Šaman and Pavel Fiedler

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


A general and versatile synthetic approach to a broad series of aromatic triynes as precursors to helicene derivatives has been developed. Employing a set of simple tools, triynes comprising the (phenylethynyl)benzene, 1-(phenylethynyl)naphthalene, and 1-(1-naphthylethynyl)- naphthalene moiety have been prepared in good to excellent yields throughout the whole reaction sequence. The methodology allows constructing various types of a junction between the central diarylacetylene moiety and the attached acetylene units to get the target triynes of general formula R-C≡C-CH2-X-CH2-Ar-C≡C-Ar'-CH2-X-CH2-C≡C-R or R-C≡C-CH2CH2-Ar-C≡C-Ar'-CH2CH2-C≡C-R (R = H, CH3, TMS, or TIPS; X = O, NTs, or C(CO2CH3)2; Ar/Ar' = 2-phenylene or 2-naphthylene).

Keywords: Acetylenes; Alkynes; Arenes; Ethers; Helicenes; Sonogashira reaction; Triynes; Cyclotrimerizations; Cross-coupling reactions.

References: 69 live references.