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(2-Fluoroallyl)boration of Ketones with (2-Fluoroallyl)boronates

The Journal of Organic Chemistry. 2020. Vol. 85. No. 10. P. 6295–6308.
Novikov M., Bobrova A., Mezentsev I., Medvedev M., Tomilov Y.

Efficient routes toward activation of gem-chlorofluorocyclopropane-derived (2-fluoroallyl)boronates for allylboration of various ketones including functionalized and low-reactive ones were developed. Increasing the boron electrophilicity by the transformation of a boronate moiety into a borinic ester with nBuLi/trifluoroacetic anhydride (TFAA) makes (2-fluoroallyl)boration of acetyl arenes/hetarenes and aliphatic ketones possible with high diastereoselectivity. For low-reactive or sterically hindered ketones (e.g., benzophenone, adamantanone), “CuF”-based catalysts were developed: (NHC)CuF·HF and (NHC)CuOTf in the presence of an excess of KHF2 (NHC = IPr, SIPr, IPrCl).

Research target: Chemistry
Language: English
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Keywords: Aromatic compoundsmolecular structureKetonesMixturesorganic compounds
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