35802-50-7Relevant articles and documents
METHOD FOR PRODUCING ALLYLSILANE COMPOUND UTILIZING PALLADIUM NANOPARTICLE CATALYST
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Paragraph 0062-0097; 0101, (2020/11/24)
PROBLEM TO BE SOLVED: To provide a method for efficiently producing an allylsilane compound from a substrate being inexpensive and capable of being easily handled in one step without using a large amount of a metal catalyst. SOLUTION: The method for producing an allylsilane compound represented by formula (C) includes a reaction step of reacting an allyl alcohol compound represented by formula (A) and a disilane compound represented by formula (B) in the presence of a palladium nanoparticle catalyst having a coordinating organic compound coordinated to the surface of a palladium nanoparticle and a co-catalyst. (In formulae (A) to (C), R1 to R3 each independently represent a hydrogen atom, a 1-20C aliphatic hydrocarbon group, a 6-20C aromatic hydrocarbon group or a 3-20C aromatic heterocyclic group; R4 and R5 each independently represent a hydrogen atom, 1-20C aliphatic hydrocarbon group, a 6-20C aromatic hydrocarbon group or a 3-20C aromatic heterocyclic group; and R6 to R8 each independently represent a hydrogen atom, a halogen atom, a 1-20C aliphatic hydrocarbon group or a 6-20C aromatic hydrocarbon group.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT
METHOD FOR PRODUCING ALLYLSILANE COMPOUND
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Paragraph 0027; 0031; 0034; 0038; 0042, (2017/09/19)
PROBLEM TO BE SOLVED: To provide a method for producing an allylsilane compound which can efficiently produce an allylsilane compound. SOLUTION: An allylsilane compound can be efficiently produced by the reaction between a halogenated allyl compound and a disilane compound in the presence of a palladium element-containing nanoparticle having solvent coordinated on the surface. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2017,JPOandINPIT
Regioselectivity of Stoichiometric Metathesis of Vinylsilanes with Second-Generation Grubbs Catalyst: A Combined DFT and Experimental Study
?liwa, Pawe?,Kurleto, Kamil,Handzlik, Jaros?aw,Rogalski, Szymon,Zak, Patrycja,Wyrzykiewicz, Bozena,Pietraszuk, Cezary
supporting information, p. 621 - 628 (2016/03/25)
The regioselectivity of metathesis reactions of trisubstituted vinylsilanes H2C=CHSiR3 (SiR3 = SiCl3, SiCl2Me, SiClMe2, SiMe3, Si(OEt)3) with the second-generation rut
Pd-catalyzed synthesis of allylic silanes from allylic ethers
Moser, Ralph,Nishikata, Takashi,Lipshutz, Bruce H.
supporting information; experimental part, p. 28 - 31 (2010/03/03)
Chemical Equation Presented Allylic phenyl ethers serve as electrophiles toward Pd(O) en route to a variety of allylic silanes. The reactions can be run at room temperature in water as the only medium using micellar catalysis
Scope and limitation of the [1,2]-phenylsulfanyl (PhS) migration in the synthesis of tetrahydrofurans and tetrahydropyrans from common triol precursors
House, David,Kerr, Fraser,Warren, Stuart
, p. 2652 - 2662 (2007/10/03)
Scope and limitation of the [1,2]-phenylsulfanyl (PhS) migration in the synthesis of tetrahydrofurans and tetrahydropyrans from common triol precursors were discussed. Triols containing three secondary hydroxy groups were rearranged using either toluene-p
Formation of allylsilanes from Cl2[P(C6H11)3]2Ru=C(R)H and vinylsilanes - β-SIR'3 elimination from ruthenacyclobutanes as a terminating step in olefin cross-metathesis
Pietraszuk,Fischer
, p. 2463 - 2464 (2007/10/03)
Stoichiometric reactions of the Grubbs carbene complex [Cl2{P(C6H11)3}2Ru=C(Ph)H] with vinylsilanes, H2C=C(Si-Me(n)R(3-n))H (R = Ph, OEt; n = 1, 2, 3), afford metathesis products and allylsilanes formed by β-SiR3 elimination followed by reductive elimination; the formation of allylsilanes constitutes a terminating step in the Ru-catalysed cross-metathesis of olefins with methylsubstituted vinylsilanes.
Regio- and Stereochemistry on the Electrophilic Trapping of Allylic Samariums Generated by Reductive Cleavage of Allylic Ethers with (C5Me5)2Sm(thf)n
Takaki, Ken,Kusudo, Takeshi,Uebori, Shinya,Nishiyama, Tetsushi,Kamata, Tohru,Yokoyama, Masaki,Takehira, Katsuomi,Makioka, Yoshikazu,Fujiwara, Yuzo
, p. 4299 - 4304 (2007/10/03)
The C-O bond of allylic benzyl ethers was selectively cleaved with Cp*2Sm(thf)n to give allylic samarium complexes in good yields. Facility of their bond fission has been found to be comparable to that of the corresponding propargylic ethers intermolecularly, but lower intramolecularly. Regio-and stereochemistry on the electrophilic trapping of the allylic complexes thus generated remarkably depended on the nature of the electrophiles. They reacted with carbonyl compounds exclusively from the most substituted terminus of the allylic moieties to yield blanched homoallylic alcohols with anti diasteroselectivity. On the other hand, trapping with silyl chlorides produced linear allylic silanes. Here, a plausible mechanism to account for the difference is proposed.
Palladium-Catalyzed Silylation of Allylic Acetates with Hexamethyldisilane or (Trimethylsilyl)tributylstannane
Tsuji, Yasushi,Kajita, Satoshi,Isobe, Shinya,Funato, Masahiro
, p. 3607 - 3608 (2007/10/02)
Various allylic acetates (1a-j) are silylated with hexamethyldisilane (Me3SiSiMe3, 2) in the presence of a catalytic amount of Pd(DBA)2 and LiCl at 100 deg C to afford the corresponding allylic silanes in high yields.In addition, (trimethylsilyl)tributylstannane (Me3SiSnBu3, 3) can be used for the silylation of aromatic allylic acetates 1g-j at room temperature.
REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALLYLTRIMETHYLSILANES VIA KRIEF-REICH ELIMINATION IN β-SELENO-γ-SILYL ALCOHOLS
Sarkar, Tarun K.,Ghosh, Sunil K.,Satapathi, Tushar K.
, p. 1885 - 1898 (2007/10/02)
The synthesis of (E)-allyltrimethylsilanes by regio- and stereocontrolled pathways is described based on the preference for Krief-Reich elimination over silicon-controlled rearrangement in β-seleno-γ-silyl alcohols, readily available from α-selenoaldehydes, 10 - 12.Usefulness of this protocol for the introduction of the allylsilane function α to the carbonyl group in cycloalkanones as well as for the preparation of unsymmetrically substituted allylsilanes is also reported.
Regioselective Synthesis of Allyltrimethylsilanes from Allylic Halides and Allylic Sulfonates. Application to the Synthesis of 2,3-Bis(trimethylsilyl)alk-1-enes
Smith, Janice Gorzynski,Drozda, Susan E.,Petraglia, Susan P.,Quinn, Nina R.,Rice, Elizabeth M.,et al.
, p. 4112 - 4120 (2007/10/02)
The preparation of allyltrimethylsilanes by regioselective pathways is described.Treatment of (E)-1-chloro-2-alkenes with a reagent prepared from 1 equiv each of trimethylsilyllithium and copper(I) iodide in hexamethylphosphoramide to presumably form a (trimethylsilyl)copper reagent affords 3-(trimethylsilyl)-1-alkenes in good to excellent yields with a high regioselectivity.Treatment of these same 1-chloro-2-alkenes with (trimethylsilyl)lithium alone without added copper(I) iodide yields only (E)-1-(trimethylsilyl)-2-alkenes.A single allylic halide thus yields two regioisomeric allyltrimethylsilanes by proper choice of reaction conditions.The reaction of a variety of allylic sulfonates with (trimethylsilyl)copper has also been investigated.The mesylates of 2 deg and 3 deg allylic alcohols yield mixtures of isomeric allyltrimethylsilanes in which the 1-(trimethylsilyl)-2-alkenes predominate.With geraniol, the mesylate was prepared in situ and allowed to react with (trimethylsilyl)copper to afford two isomeric allyltrimethylsilanes in which the 3-(trimethylsilyl)-1-alkene predominates.Finally, these reactions have also been used to prepare a variety of 2,3-bis(trimethylsilyl)alk-1-enes, a class of unsaturated organosilanes which has received little attention in the literature.
