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Alkynylboration has been achieved in the reaction of alkynyl(pinacol)boranes with alkynes in the presence of nickel catalysts, giving cis-1-borylbut-1-en-3-yne derivatives. 1-Aryl-1-alkynes underwent the alkynylboration regioselectively with the selective introduction of the alkynyl groups at their 1-positions, where the aryl groups were attached. The boryl-substituted enynes were reacted with sp2 halides under the Suzuki-Miyaura coupling conditions, giving highly conjugated enynes in high yields.
Suginome et al. (Tue,) studied this question.