An efficient set of NHC (N-heterocyclic carbine)-Cu-catalyzed protocols for site-selective boron-copper addition to terminal alkynes to efficiently afford a-vinylboronates is presented. Propargyl alcohol and amine, and their derivatives are effective substrates for this transformation, and a variety of aryl-substituted terminal alkynes are also suitable class of substrates. Mechanistic studies are presented, which indicate that both the structural and electronic features of the NHCs and alkyne substrates affect the a selectivity.

Highly selective methods for synthesis of internal (α-) vinylboronates through efficient NHC−Cu-catalyzed hydroboration of terminal alkynes

243rd National Meeting (2012)

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