B(C6F5)3-Catalyzed Hydroarylation of Terminal Alkynes with Phenols

We developed a B(C6F5)(3) catalyzed hydroarylation of terminal alkynes with various phenols at room temperature without adding any additives, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. Those transformations featured a broad substrate scope with moderate yields. Mechanism studies indicated that those transformations proceeded through the activation of phenol by B(C6F5)(3) with subsequent protonation of alkyne/Friedel-Crafts-type reaction.

Automated summary

A B(C6F5)(3)-catalyzed hydroarylation of terminal alkynes with various phenols at room temperature was developed, leading to the synthesis of 2-gem-vinylphenols with good regio-selectivity. The transformations exhibited a broad substrate scope with moderate yields, and mechanism studies suggested the activation of phenol by B(C6F5)(3) followed by protonation of the alkyne/Friedel-Crafts-type reaction.