17739-53-6Relevant academic research and scientific papers
Metal-free hydrogen evolution cross-coupling enabled by synergistic photoredox and polarity reversal catalysis
Cao, Jilei,Lu, Kanghui,Ma, Lishuang,Yang, Xiaona,Zhou, Rong
supporting information, p. 8988 - 8994 (2021/11/23)
A synergistic combination of photoredox and polarity reversal catalysis enabled a hydrogen evolution cross-coupling of silanes with H2O, alcohols, phenols, and silanols, which afforded the corresponding silanols, monosilyl ethers, and disilyl ethers, respectively, in moderate to excellent yields. The dehydrogenative cross-coupling of Si-H and O-H proceeded smoothly with broad substrate scope and good functional group compatibility in the presence of only an organophotocatalyst 4-CzIPN and a thiol HAT catalyst, without the requirement of any metals, external oxidants and proton reductants, which is distinct from the previously reported photocatalytic hydrogen evolution cross-coupling reactions where a proton reduction cocatalyst such as a cobalt complex is generally required. Mechanistically, a silyl cation intermediate is generated to facilitate the cross-coupling reaction, which therefore represents an unprecedented approach for the generation of silyl cationviavisible-light photoredox catalysis.
Synthesis and kinetics of disassembly for silyl-containing ethoxycarbonyls using fluoride ions
Camerino, Eugene,Daniels, Grant C.,Wynne, James H.,Iezzi, Erick B.
, p. 1884 - 1888 (2018/02/06)
In this study, a series of silyl-containing ethoxycarbonates and ethoxycarbamates on electron poor anilines and phenols were synthesized and their kinetics of disassembly determined in real-time upon exposure to fluoride ion sources at room temperature. The results provide a greater understanding of stability and kinetics for silyl-containing protecting groups that eliminate volatile molecules upon removal, which will allow for simplification of orthogonal protection in complex organic molecules.
Instantaneous Conversion of [11C]CO2 to [11C]CO via Fluoride-Activated Disilane Species
Taddei, Carlotta,Bongarzone, Salvatore,Gee, Antony D.
supporting information, p. 7682 - 7685 (2017/06/06)
The development of a fast and novel methodology to generate carbon-11 carbon monoxide ([11C]CO) from cyclotron-produced carbon-11 carbon dioxide ([11C]CO2) mediated by a fluoride-activated disilane species is described. This methodology allows up to 74 % conversion of [11C]CO2 to [11C]CO using commercially available reagents, readily available laboratory equipment and mild reaction conditions (room temperature). As proof of utility, radiochemically pure [carbonyl-11C]N-benzylbenzamide was successfully synthesized from produced [11C]CO in up to 74 % radiochemical yield (RCY) and >99 % radiochemical purity (RCP) in ≤10 min from end of [11C]CO2 delivery.
Facile synthesis of cyclic fluorosiloxanes
Oguri, Naoki,Takeda, Nobuhiro,Unno, Masafumi
supporting information, p. 1506 - 1508 (2015/11/24)
Novel 1,3,5,7-tetrafluorocyclotetrasiloxanes were synthesized from cyclotetrasiloxanetetraol by a facile synthetic method. By adjusting the amount of the fluorinating reagent, synthesis of a single isomer of 1,3,5,7-tetrafluorocyclotetrasiloxanes as well as the preparation of all four isomers were accomplished. The products are expected to serve as potential precursors to not only well-defined silsesquioxanes but also asymmetric cyclic siloxanes.
Meerwein's reagent mediated, significantly enhanced nucleophilic fluorination on alkoxysilanes
Jorapur, Yogesh R.,Shimada, Toyoshi
supporting information; experimental part, p. 1064 - 1068 (2012/06/17)
We developed a new facile method to fluorosilanes from alkoxysilanes using Meerwein's reagent. Our protocol afforded fluorosilanes in excellent yields in various organic solvents including acetonitrile under mild reaction conditions at room temperature. We also proposed a reaction mechanism with the probable silyloxonium intermediates. Georg Thieme Verlag Stuttgart · New York.
Selective synthesis of halosilanes from hydrosilanes and utilization for organic synthesis
Kunai, Atsutaka,Ohshita, Joji
, p. 3 - 15 (2007/10/03)
Selective synthesis of halosilanes has been examined. Various types of halosilanes and halohydrosilanes, such as R3SiX, R2SiHX, R2SiX2, RSiH2X, RSiHX2 (X=Cl, Br, F), were obtained by the reactions of the corresponding hydrosilanes with Cu(II)-based reagents selectively in high yields. This method could be also applied to the synthesis of chlorofluorosilanes and chlorohydrogermanes. On the other hand, iodo- and bromosilanes and germanes were obtained by Pd- or Ni-catalyzed hydride-halogen exchange reactions of hydrosilanes with alkyl or allyl halides. Their synthetic applications have been demonstrated by using iodo- and bromosilanes and chlorofluorosilanes.
Synthesis, structure, and reactivity of 1,ω-bis(pseudo-pentacoordinated) 1,ω-difluoro-oligosilanes bearing 8-(dimethylamino)-1-naphthyl groups
Tamao, Kohei,Asahara, Masahiro,Sun, Guang-Ri,Kawachi, Atsushi
, p. 193 - 205 (2007/10/03)
1,ω-Bis[8-(dimethylamino)-1-naphthyl]-1,ω-difluorotrisilane 1 (ω=3) and tetrasilane 2 (ω=4) have been prepared. The X-ray crystallography of dl-1 and meso-1 shows unsymmetrical structures having different coordination modes at the two terminal silicons. T
2-DIPHENYLMETHYLSILYLETHYL GROUP AS A NEW PROTECTING GROUP OF INTERNUCLEOTIDIC PHOSPHATES IN OLIGONUCLEOTIDE SYNTHESIS
Honda, Shinkichi,Hata, Tsujiaki
, p. 2093 - 2096 (2007/10/02)
Internucleotidic phosphates were protected by 2-diphenylmethylsilylethyl group which was selectively removed by treatment with tetrabutylammonium fluoride.
