Journal of the American Chemical Society p. 8532 - 8535 (2014)
Update date:2022-08-04
Topics:
Nagashima, Yuki
Hirano, Keiichi
Takita, Ryo
Uchiyama, Masanobu
We present the first trans-selective diborylation reaction of alkynes. By means of theoretical calculation-assisted reaction analysis, we designed a pseudo-intramolecular reaction of diboron, propargyl alcohol, and a base to facilitate B-B bond activation and C-B bond formation with high efficiency. This approach provides synthetically versatile and densely functionalized 4-borylated 1,2-oxaborol-2(5H)-oles (vinyldiboronates) in a straightforward manner. Detailed computational analysis showed that the directing alkoxide functionality markedly lowers the activation energy of B-C bond formation.
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