Topic
Triethylsilane
About: Triethylsilane is a research topic. Over the lifetime, 989 publications have been published within this topic receiving 17605 citations.
Papers published on a yearly basis
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Papers
TL;DR: A robust, living tandem catalytic system for the deoxygenative reduction of CO(2) to CH(4) and resumed hydrosilylation is indicated.
Abstract: The frustrated Lewis pair system consisting of 2 equiv of 2,2,6,6-tetramethylpiperidine (TMP) and tris(pentafluorophenyl)borane [B(C6F5)3] activates carbon dioxide to form a boratocarbamate−TMPH ion pair. In the presence of triethylsilane, this species is converted to a silyl carbamate and the known ion pair [TMPH]+[HB(C6F5)3]−, which recently was shown to react with CO2 via transfer of the hydride from the hydridoborate to form the formatoborate [TMPH]+[HC(O)OB(C6F5)3]−. In the presence of extra B(C6F5)3 (0.1−1.0 equiv) and excess triethylsilane, the formatoborate is rapidly hydrosilated to form a formatosilane and regenerate [TMPH]+[HB(C6F5)3]−. The formatosilane in turn is rapidly hydrosilated by the B(C6F5)3/Et3SiH system to CH4, with (Et3Si)2O as the byproduct. At low [Et3SiH], intermediate CO2 reduction products are observed; addition of more CO2/Et3SiH results in resumed hydrosilylation, indicating that this is a robust, living tandem catalytic system for the deoxygenative reduction of CO2 to CH4.
469 citations
TL;DR: In this paper, the removal of thiocarbonylthio groups from polymers synthesized by radical polymerization with reversible addition−fragmentation chain transfer (RAFT) by radical-induced reduction has been studied.
Abstract: The removal of thiocarbonylthio groups from polymers synthesized by radical polymerization with reversible addition−fragmentation chain transfer (RAFT) by radical-induced reduction has been studied. The efficiency of reduction is strongly dependent on the H-donor and the polymer. The effectiveness of the H atom donors studied increases in the series toluene ≪ 2-propanol < triethylsilane < triphenylsilane ≪ tris(trimethylsilyl)silane ∼ N-ethylpiperidine hypophosphite < tributylstannane. The end groups of the (meth)acrylic polymers, e.g., poly(butyl acrylate) and poly(methyl methacrylate), are more readily reduced than those of polystyrene. With poor H-donors such as toluene or 2-propanol radical−radical reaction between propagating radicals competes with reduction even when they are used in vast excess as a solvent for the process. Thiocarbonylthio groups of polymers prepared with dithiobenzoate or trithiocarbonate RAFT agents can be replaced by hydrogen by radical-induced reduction with hypophosphite salt...
256 citations
TL;DR: This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature.
Abstract: This communication describes a metal-free methodology involving an efficient and controlled reduction of secondary amides to imines, aldehydes, and amines in good to excellent yields under ambient pressure and temperature. The process includes a chemoselective activation of a secondary amide with triflic anhydride in the presence of 2-fluoropyridine. The electrophilic activated amide can then be reduced to the corresponding iminium using triethylsilane, a cheap, rather inert, and commercially available reagent. Imines can be isolated after a basic workup or readily transformed to the aldehydes following an acidic workup. The amine moiety can be accessed via a sequential reductive amination by the addition of silane and Hantzsch ester hydride in a one-pot reaction. Moreover, this reduction tolerates various functional groups that are usually reactive under reductive conditions and is very selective to secondary amides.
252 citations
TL;DR: Triethylsilane was used as a scavenging agent in peptide synthesis for the removal of protecting groups with TFA as discussed by the authors, and the efficiency of scavenging ability was compared with anisole and ethanedithiol in a kinetic experiment.
240 citations
TL;DR: In situ generation of molecular hydrogen by addition of triethylsilane to palladium-charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.
Abstract: In situ generation of molecular hydrogen by addition of triethylsilane to palladium-charcoal catalyst results in rapid and efficient reduction of multiple bonds, azides, imines, and nitro groups, as well as benzyl group and allyl group deprotection under mild, neutral conditions.
212 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2025 | 1 |
| 2024 | 5 |
| 2023 | 8 |
| 2022 | 11 |
| 2021 | 20 |
| 2020 | 11 |