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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 authored 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.