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Title: A versatile NHC-parent silyliumylidene cation for catalytic chemo- and regioselective hydroboration
Authors: Leong, Bi-Xiang
Lee, Jiawen
Li, Yan
Yang, Ming-Chung
Siu, Chi-Kit
Su, Ming-Der
So, Cheuk-Wai
Keywords: Science::Chemistry
Issue Date: 2019
Source: Leong, B., Lee, J., Li, Y., Yang, M., Siu, C., Su, M. & So, C. (2019). A versatile NHC-parent silyliumylidene cation for catalytic chemo- and regioselective hydroboration. Journal of the American Chemical Society, 141(44), 17629-17636.
Journal: Journal of the American Chemical Society
Abstract: This study describes the first use of a silicon(II) complex, NHC-parent silyliumylidene cation complex [(IMe)2SiH]I (1, IMe = :C{N(Me)C(Me)}2) as a versatile catalyst in organic synthesis. Complex 1 (loading: 10 mol %) was shown to act as an efficient catalyst (reaction time: 0.08 h, yield: 94%, TOF = 113.2 h-1; reaction time: 0.17 h, yield: 98%, TOF = 58.7 h-1) for the selective reduction of CO2 with pinacolborane (HBpin) to form the primarily reduced formoxyborane [pinBOC(═O)H]. The activity is better than the currently available base-metal catalysts used for this reaction. It also catalyzed the chemo- and regioselective hydroboration of carbonyl compounds and pyridine derivatives to form borate esters and N-boryl-1,4-dihydropyridine derivatives with quantitative conversions, respectively. Mechanistic studies show that the silicon(II) center in complex 1 activated the substrates and then mediated the catalytic hydroboration. In addition, complex 1 was slightly converted into the NHC-borylsilyliumylidene complex [(IMe)2SiBpin]I (3) in the catalysis, which was also able to mediate the catalytic hydroboration.
ISSN: 0002-7863
DOI: 10.1021/jacs.9b06714
Rights: © 2019 American Chemical Society. All rights reserved.
Fulltext Permission: none
Fulltext Availability: No Fulltext
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