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 › peer-review

83 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

Keywords

carbonyl hydroboration
chemoselective hydroboration
homogeneous catalysis
ketone/aldehyde reduction
lanthanide

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1021/acscatal.6b03332

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

abstract = "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.",

keywords = "carbonyl hydroboration, chemoselective hydroboration, homogeneous catalysis, ketone/aldehyde reduction, lanthanide",

author = "Weidner, {Victoria L.} and Barger, {Christopher J.} and Massimiliano Delferro and Lohr, {Tracy L.} and Marks, {Tobin J.}",

note = "Funding Information: Financial support was provided by National Science Foundation through element grant CHE-1213235. This work made use of the IMSERC at Northwestern University, which has received support from the NSF (CHE-1048773 and CHE-9871268); Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF NNCI-1542205); the State of Illinois and International Institute for Nanotechnology. V.L.W. was supported by an NSF graduate research fellowship. We acknowledge R.J. Thomson (Northwestern) for helpful discussions.",

year = "2017",

month = feb,

day = "3",

doi = "10.1021/acscatal.6b03332",

language = "English",

volume = "7",

pages = "1244--1247",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "2",

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T1 - Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst

AU - Weidner, Victoria L.

AU - Barger, Christopher J.

AU - Delferro, Massimiliano

AU - Lohr, Tracy L.

AU - Marks, Tobin J.

N1 - Funding Information: Financial support was provided by National Science Foundation through element grant CHE-1213235. This work made use of the IMSERC at Northwestern University, which has received support from the NSF (CHE-1048773 and CHE-9871268); Soft and Hybrid Nanotechnology Experimental (SHyNE) Resource (NSF NNCI-1542205); the State of Illinois and International Institute for Nanotechnology. V.L.W. was supported by an NSF graduate research fellowship. We acknowledge R.J. Thomson (Northwestern) for helpful discussions.

PY - 2017/2/3

Y1 - 2017/2/3

N2 - 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.

AB - 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.

KW - carbonyl hydroboration

KW - chemoselective hydroboration

KW - homogeneous catalysis

KW - ketone/aldehyde reduction

KW - lanthanide

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JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

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

Abstract

Keywords

ASJC Scopus subject areas

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