119873-74-4Relevant academic research and scientific papers
Divergent Synthesis of Vinyl-, Benzyl-, and Borylsilanes: Aryl to Alkyl 1,5-Palladium Migration/Coupling Sequences
Han, Jie-Lian,Ju, Cheng-Wei,Qin, Ying,Zhao, Dongbing
supporting information, p. 6555 - 6560 (2020/03/03)
Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through-space metal/hydrogen shifts allow functionalization of C?H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5-palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl-, benzyl-, and borylsilanes, constituting a unique C(sp3)?H transformation based on a 1,5-palladium migration process.
Highly selective oxidation of organosilanes to silanols with hydrogen peroxide catalyzed by a lacunary polyoxotungstate
Ishimoto, Ryo,Kamata, Keigo,Mizuno, Noritaka
supporting information; experimental part, p. 8900 - 8904 (2010/01/16)
Silanol synthesis: Divacant lacunary polyoxotungstate (nBu4N+)4[g- SiW10O34(H2O)2] (I) is an efficient homogeneous catalyst for highly selective oxidation of organosilanes to silanols with 30/60% aqueous H2O2. Various kinds of silanes 1 containing aryl, alkyl, alkenyl, alkynyl and alkoxy groups are chemoselectively converted into the corresponding silanols 2 in high yields with only one equivalent of aqueous H2O2 with respect to the substrate.
Highly Efficient Iridium-Catalyzed Oxidation of Organosilanes to Silanols
Lee, Youngjun,Seomoon, Dong,Kim, Sundae,Han, Hoon,Chang, Sukbok,Lee, Phil Ho
, p. 1741 - 1743 (2007/10/03)
Hydrolytic oxidation of organosilanes to the corresponding silanols can be performed highly efficiently with a catalyst system of [IrCl(C8H 12)]2 under essentially neutral and mild conditions, and various types of silanols are produced in good to excellent yields.
[RuCl2(p-cymene)]2 on carbon: An efficient, selective, reusable, and environmentally versatile heterogeneous catalyst
Choi, Eunjung,Lee, Chongmok,Na, Youngim,Chang, Sukbok
, p. 2369 - 2371 (2007/10/03)
(Matrix Presented) A heterogeneous ruthenium catalyst, easily prepared by adsorption of [RuCl2(p-cymene)]2 on activated carbon, exhibited a highly efficient and selective catalytic activity in various environmentally attractive transformations such as aerobic oxidation, hydrolytic oxidation, and dehydration processes with excellent recyclability.
A facile preparation and cyclopropanation of 1-alkenylsilanols
Hirabayashi, Kazunori,Takahisa, Eisuke,Nishihara, Yasushi,Mori, Atsunori,Hiyama, Tamejiro
, p. 2409 - 2417 (2007/10/03)
Alkenylsilanols are prepared by the reaction of hexamethyltrisiloxane (D3) with alkenyllithiums or alternatively by the reaction of cyclic siloxanes substituted by an alkenyl group with organolithiums and transformed to the corresponding cyclopropylsilanols using diiodomethane and diethylzinc. Lithium alkenylsilanolates, primary products of the preparation, also undergo cyclopropanation. As in the case of allylic alcohols, the silanol functionality is found to enhance the rate of cyclopropanation compared with that of alkenyltrialkylsilane or alkoxydialkylsilane. The obtained cyclopropylsilanols are further converted into the corresponding cyclopropanols by the Tamao oxidation.
Competitive acylation of arylstyrylsilanes: Controlling silanucleophile reactivity
Brook, Michael A.,Henry, Courtney
, p. 861 - 868 (2007/10/03)
Electrophilic substitution reactions occurred cleanly between acyl cations and arylstyrylsilanes 2-4. With an unsubstituted aryl group, 2 underwent transfer of the styryl group to form styryl ketone 5 as would be predicted from previous kinetic studies. With increasing methyl group substitution of the aryl group, aryl group transfer occurred competitively such that 3 showed a 2:1 preference for destyrylation: dearylation giving 10:11 while 4 underwent exclusive transfer of the mesityl group to give mesityl ketones 6-8. These results are not consistent with electrophilic aromatic substitution reactions of nonsilylated compounds. With increasing methyl group substitution of the aryl group, its reactivity should increase for electronic reasons but not to the extent that is surpasses that of the styryl group. When the silyl group is flanked by methyl groups, however, cleavage of the silicon-aryl bond is additionally facilitated by the relief of steric congestion such that this process occurs preferentially to transfer of the styryl group.
Enantioselective synthesis of epoxides via Sharpless epoxidation of alkenylsilanols
Chan, T. H.,Chen, L. M.,Wang, D.,Li, L. H.
, p. 60 - 67 (2007/10/02)
Enantioselective synthesis of simple epoxides can be achieved by Sharpless epoxidation of alkenylsilanols followed by protodesilylation of the chiral epoxysilanols.The approach has been applied to the synthesis of frontalin.
Enantioselective Synthesis of Epoxides: Sharpless Epoxidation of Alkenysilanols
Chan, T. H.,Chen, L. M.,Wang, D.
, p. 1280 - 1281 (2007/10/02)
Sharpless epoxidation of the alkenylsilanol (6) followed by protodesilylation gave styrene oxide with high enentiomeric excess.
