Pan, X and Boussonnière, A and Curran, DP
(2013)
Molecular iodine initiates hydroborations of alkenes with N-heterocyclic carbene boranes.
Journal of the American Chemical Society, 135 (38).
14433 - 14437.
ISSN 0002-7863
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Abstract
The hydroboration of alkenes of diverse structural types by assorted N-heterocyclic carbene boranes can be accomplished by addition of 5-10% diiodine. For example, reaction of 1,3-dimethylimidazol-2-ylidene borane (diMe-Imd-BH3) with 10% I2 followed by addition of 2,3-dimethyl-2-butene provided the corresponding thexyl NHC-borane (diMe-Imd-BH2thexyl) in 75% yield. This and related monohydroboration products are stable to chromatography and storage. The scope of the new reaction is described, and the mechanism is probed by 11B NMR experiments. © 2013 American Chemical Society.
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