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.
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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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 -