New protocol for one-pot synthesis of functionalized symmetrical 1,4-dialkyl- or 1,4-diaryl-1,3-diynes

• A one-pot protocol for synthesis of functionalized 1,4-disubstituted-1,3-diynes was elaborated.
• Catalytic silylative coupling of terminal alkynes with (vinyl-)iodosilanes was adopted as first sequence reactions.
• The catalytic conditions for the copper salt mediated homocoupling of trimethylsilylalkyne were established.

A new versatile one-pot protocol for preparation of functionalized 1,4-disubstituted-1,3-diynes via a highly selective catalytic silylative coupling of vinylsilanes and terminal alkynes occurring via [Ru] catalyzed reaction and/or [Ir] catalyzed reaction of iodosilanes with alkynes followed by desilylative homocoupling sequence is presented. Contrary to existing stoichiometric systems, the catalytic conditions for the copper salt mediated homocoupling of trimethylsilylalkyne were elaborated that are very tolerant to various functional groups.

A new, effective route to functionalized 1,4-disubstituted-1,3-diynes via a sequence of two catalytic reactions, i.e. silylative coupling and desilylative homocoupling is presented. First of the processes is the [Ru]-catalyzed reaction of terminal alkynes and vinylsilanes or [Ir]-catalyzed reaction of iodosilanes with alkynes followed by copper salt mediated homocoupling of trimethylsilylalkyneFigure optionsDownload as PowerPoint slide