1,3-Diynes are characterized by the unique rod-like structure and are widely used to synthesize biologically active molecules, polymers, and supramolecular tools. Access to borylated 1,3-diynes provides a new avenue for further transformation since boronic acid derivatives are well-established synthetic intermediates. Herein, we report a metal-free, organocatalytic method for the trans hydroboration of 1,3-diynes with pinacolborane to afford (E)-1-boryl-1,3-enynes (Scheme 1). The reaction proceeds with excellent regio- and stereo-selectivity, which is unambiguously established from NMR and X-ray crystallography studies. The products are afforded in high yields up to 95% and apply to a broad substrate scope. The experimental and theoretical studies regarding a plausible mechanism will be discussed.

Transition metal-free regio- and stereo- selective trans hydroboration of 1,3-diynes: Phosphine catalyzed access to borylated 1,3-enynes

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