Abstract A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.

This study developed a transition metal-free method for semi-reduction of alkynoic acids through an -borylation and protodeborylation sequence, yielding aryl acrylic acids with a dual role for the carboxylate anion.

Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence

Key Takeaway: This study developed a transition metal-free method for semi-reduction of alkynoic acids through an -borylation and protodeborylation sequence, yielding aryl acrylic acids with a dual role for the carboxylate anion.