Highly Efficient and Chemoselective Zinc‐Catalyzed Hydrosilylation of Esters under Mild Conditions

Kovalenko, Oleksandr O.; Adolfsson, Hans

doi:10.1002/chem.201406176

Cited by 37 publications

(14 citation statements)

References 64 publications

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“…Alcohol 3a was obtained as a white solid (106 mg, 78%), with 97% purity (according to HPLC, R t 4.27 min). The spectral data was in accordance with these reported in literature .…”

Section: Methodssupporting

confidence: 91%

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Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

Niezgoda¹,

Gliszczyńska²,

Kempińska

et al. 2017

Euro J Lipid Sci & Tech

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Conjugated linoleic acid (CLA) is natural unsaturated fatty acid known for the wide biological properties therefore is available in functional food and cosmetics and as a dietary supplements. In this study a series of simple derivatives of cis-9,trans-11 and trans-10,cis-12 CLA and a mixture of those isomers have been proposed as alternative for free CLA preparations. Obtained in high yields (>72%) ethyl esters, alcohols and their acetates have been subjected to in vitro cytotoxic assay against human tumor cells (human promyelocytic leukemia, breast cancer and colon cancer) and compered with stearic and linoleic derivatives. Studies showed that the growth inhibitory activities depended on the degree of unsaturation. All CLA derivatives except ethyl esters showed similar activities compared to free CLA isomers. Moreover, this study showed that trans-10,cis-12 CLA derivatives have better anticancer properties against all tested tumour cells than derivatives of cis-9,trans-11 isomer and a mixture of both isomers. Practical applications:This paper make a contribution in the field of study of biological activity of CLA derivatives and completes deficiencies in spectroscopic data of known isomers of ethyl esters of CLA isomers, conjugated octadecadienoic alcohols and their acetates. Obtained compounds can be used as a components of cosmetics and food supplements.

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“…Alcohol 3a was obtained as a white solid (106 mg, 78%), with 97% purity (according to HPLC, R t 4.27 min). The spectral data was in accordance with these reported in literature .…”

Section: Methodssupporting

confidence: 91%

“…Obtained fatty alcohols ( 3a–e ) were analyzed by HPLC and NMR. Compounds 3a–e are known in the literature , however their spectroscopic data are not complete so the full 1 H and 13 C NMR characteristics are presented in Supplementary material.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

Niezgoda¹,

Gliszczyńska²,

Kempińska

et al. 2017

Euro J Lipid Sci & Tech

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“…In addition, reduction of conjugated systems such as the methyl cinnamate gave a complex mixture of products. Substrate limitations have also been encountered by Turculet and co‐workers using the manganese complex [(k 2 ‐P,N)Mn(N(SiMe 3 ) 2 ], and have been described with iron‐based catalysts …”

Section: Resultsmentioning

confidence: 99%

Bench‐Stable Manganese NHC Complexes for the Selective Reduction of Esters to Alcohols with Silanes

2020

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Selective reduction of esters to alcohols was accomplished through Mn(I)‐mediated hydrosilylation reaction. The manganese tricarbonyl complex [Mn(bis‐NHC)(CO)3Br] resulted an active pre‐catalyst for the reduction of a variety of esters using phenylsilane and the cheap and readily available polymethylhydrosiloxane. An in situ examination of the catalytic reaction using 55Mn NMR spectroscopy allowed us to detect the formation of Mn(I) intermediate active species.

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“…[5] Indeed,t his strategy enables the formation of silyl acetals,w hich can be converted to aldehydes upon hydrolysis. Althought he hydrosilylation reaction has been successful for the selective reduction of esterst oa lcohols or ethers, [6,7] examples of hydrosilylation of esterst oa ldehydes are scarce. [8] Af irst example using ar utheniumc arbonyl catalysta th igh temperature showedar ather narrow substrate scope.…”

Section: Introductionmentioning

confidence: 99%

Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations

Corre

Rysak

Capet

et al. 2016

Chemistry A European J

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The combination of an iridium(III) metallacycle and 1,3,5-trimethoxybenzene catalyses rapidly and selectively the reduction of esters to aldehydes at room temperature with high yields through hydrosilylation followed by hydrolysis. The ester reduction involves the trapping of transient silyl cations by the 1,3,5-trimethoxybenzene co-catalyst, supposedly by formation of an arenium intermediate whose role was addressed by DFT calculations.

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Highly Efficient and Chemoselective Zinc‐Catalyzed Hydrosilylation of Esters under Mild Conditions

Cited by 37 publications

References 64 publications

Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

Synthesis and evaluation of cytotoxic activity of conjugated linoleic acid derivatives (esters, alcohols, and their acetates) toward cancer cell lines

Bench‐Stable Manganese NHC Complexes for the Selective Reduction of Esters to Alcohols with Silanes

Selective Hydrosilylation of Esters to Aldehydes Catalysed by Iridium(III) Metallacycles through Trapping of Transient Silyl Cations

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