cs6b03332_si_001.pdf (2.06 MB)
Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst
journal contribution
posted on 2017-01-09, 00:00 authored by Victoria
L. Weidner, Christopher J. Barger, Massimiliano Delferro, Tracy L. Lohr, Tobin J. MarksRapid,
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.