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

Victoria L. Weidner; Christopher J. Barger; Massimiliano Delferro; Tracy L. Lohr; Tobin J Marks

doi:10.1021/acscatal.6b03332

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

Victoria L. Weidner, Christopher J. Barger, Massimiliano Delferro, Tracy L. Lohr, Tobin J Marks

Northwestern University

Research output: Contribution to journal › Article

61 Citations (Scopus)

Abstract

Rapid, clean hydroboration of ketones and aldehydes with HBpin is achieved using the homoleptic rare-earth catalyst La[N(SiMe₃)₂]₃ (La^NTMS). The reaction employs low catalyst loadings (0.01-1 mol % La^NTMS), 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.

Original language	English
Pages (from-to)	1244-1247
Number of pages	4
Journal	ACS Catalysis
Volume	7
Issue number	2
DOIs	https://doi.org/10.1021/acscatal.6b03332
Publication status	Published - Feb 3 2017

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Keywords

carbonyl hydroboration
chemoselective hydroboration
homogeneous catalysis
ketone/aldehyde reduction
lanthanide

ASJC Scopus subject areas

Catalysis

Cite this

Weidner, V. L., Barger, C. J., Delferro, M., Lohr, T. L., & Marks, T. J. (2017). Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst. ACS Catalysis, 7(2), 1244-1247. https://doi.org/10.1021/acscatal.6b03332

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Access to Document

10.1021/acscatal.6b03332