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Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst

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journal contribution
posted on 09.01.2017, 00:00 by Victoria L. Weidner, Christopher J. Barger, Massimiliano Delferro, Tracy L. Lohr, Tobin J. Marks
Rapid, clean hydroboration of ketones and aldehydes with HBpin is achieved using the homoleptic rare-earth catalyst La­[N­(SiMe3)2]3 (LaNTMS). The reaction employs low catalyst loadings (0.01–1 mol % LaNTMS), proceeds rapidly (>99% in 5 min) at 25 °C, and is moderately air-tolerant. Additionally, this hydroboration has good functional group compatibility, including halides, nitro groups, and nitriles, and is exclusively carbonyl-selective in the presence of alkenes and alkynes.