Journal
ACS CATALYSIS
Volume 7, Issue 2, Pages 1244-1247Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.6b03332
Keywords
homogeneous catalysis; carbonyl hydroboration; ketone/aldehyde reduction; lanthanide; chemoselective hydroboration
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Funding
- National Science Foundation [CHE-1213235]
- NSF
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1464488] Funding Source: National Science Foundation
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Rapid, clean hydroboration of ketones and aldehydes with HBpin is achieved using the homoleptic rare-earth catalyst La[N-(SiMe-3)-2](3) (La-NTMS). The reaction employs low catalyst loadings (0.01-1 mol % La-NTMS), proceeds rapidly (>99% in 5 min) at 25 degrees 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.
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