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A number of alkynyl pinacolboronates bearing various functional groups were synthesized according to literature methods. These were then stereoselectively reduced to the cis-alkenyl pinacolboronates via hydroboration with dicyclohexylborane followed by chemoselective protodeboronation using acetic acid. Treatment with potassium hydrogen fluoride smoothly converted these to the corresponding potassium organotrifluoroborates.

journal of organic chemistry

Highly Stereoselective Synthesis of <i>cis</i>-Alkenyl Pinacolboronates and Potassium <i>cis</i>-Alkenyltrifluoroborates via a Hydroboration/ Protodeboronation Approach

Highly Stereoselective Synthesis of cis-Alkenyl Pinacolboronates and Potassium cis-Alkenyltrifluoroborates via a Hydroboration/ Protodeboronation Approach