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.
| Original language | English |
|---|---|
| Pages (from-to) | 1244-1247 |
| Number of pages | 4 |
| Journal | ACS Catalysis |
| Volume | 7 |
| Issue number | 2 |
| DOIs | |
| 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
Rapid, Mild, and Selective Ketone and Aldehyde Hydroboration/Reduction Mediated by a Simple Lanthanide Catalyst. / Weidner, Victoria L.; Barger, Christopher J.; Delferro, Massimiliano; Lohr, Tracy L.; Marks, Tobin J.
In: ACS Catalysis, Vol. 7, No. 2, 03.02.2017, p. 1244-1247.Research output: Contribution to journal › Article
}
TY - JOUR
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
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
UR - http://www.scopus.com/inward/record.url?scp=85018517189&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85018517189&partnerID=8YFLogxK
U2 - 10.1021/acscatal.6b03332
DO - 10.1021/acscatal.6b03332
M3 - Article
AN - SCOPUS:85018517189
VL - 7
SP - 1244
EP - 1247
JO - ACS Catalysis
JF - ACS Catalysis
SN - 2155-5435
IS - 2
ER -