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Transition metal-free direct and base-catalyzed 1,2-diborations of arylacetylenes using pinB-BMes 2 provided a syn / anti -isomeric mixture of diborylalkenes. The kinetic analysis showed that the reaction rate and isomer ratio were affected by reaction conditions and substituents on the aryl ring. DFT calculations indicated that direct addition proceeded via the interaction of acetylene-π with the BMes 2 fragment. In contrast, for the base-catalyzed diboration, the previously isolated sp 2 -sp 3 diborane and borataallene were confirmed as stable intermediates by calculations. The whole reaction pathways can be divided into the Bpin-migration and deprotonation steps, where the borataallene should be considered as a common intermediate. It should be noted that the deprotonation step is reversible and affords the kinetically less favoured isomer under the thermodynamic conditions. As a result, the composition of isomeric products, in the base-catalyzed diboration, is attributed to the small difference of activation barriers between direct and base-catalyzed systems.

chemical science

Mechanistic study on the reaction of pinB-BMes<sub>2</sub>with alkynes based on experimental investigation and DFT calculations: gradual change of mechanism depending on the substituent

Mechanistic study on the reaction of pinB-BMes2with alkynes based on experimental investigation and DFT calculations: gradual change of mechanism depending on the substituent

Mechanistic study on the reaction of pinB-BMes₂with alkynes based on experimental investigation and DFT calculations: gradual change of mechanism depending on the substituent