109790-06-9Relevant academic research and scientific papers
Rearrangements of Organosilicon Compounds Using Organoaluminum Reagents. Conversion of Phenyl- and Alkenyl(chloromethyl)silanes to Benzyl- and Allylsilanes
Hudrlik, Paul F.,Abdallah, Yousef M.,Kulkarni, Ashok K.,Hudrlik, Anne M.
, p. 6552 - 6556 (1992)
Various (chloromethyl)silanes undergo Wagner-Meerwein-type rearrangements using a catalytic amount of EtAlCl2 in dichloromethane.The resulting chlorosilanes have been converted to alkyl(or aryl)silanes with RMgX and/or to fluorosilanes with NH4HF2.In this way phenyl-, alkenyl-, and allyl(chloromethyl)silanes were converted to benzyl-, allyl-, and homoallylsilanes, respectively.Attempted rearrangements of methyl-, alkynyl-, and furyl(chloromethyl)silanes under these conditions were not successful.
Synthesis of functionalized organoboron/silicon compounds by copper-catalyzed coupling of alkylsilyl peroxides and diboron/silylborane reagents
Seihara, Takumi,Sakurai, Shunya,Kato, Terumasa,Sakamoto, Ryu,Maruoka, Keiji
, p. 2477 - 2481 (2019)
The facile synthesis of functionalized organoboron/silicon compounds by copper-catalyzed coupling of alkylsilyl peroxides and diboron/silylborane reagents is reported. The reactions proceed smoothly under mild, neutral conditions in short reaction times t
Copper-Catalyzed Si-B Bond Activation in the Nucleophilic Substitution of Primary Aliphatic Triflates
Scharfbier, Jonas,Oestreich, Martin
, p. 1274 - 1276 (2016)
A method for the nucleophilic displacement of the triflate leaving group attached to terminally functionalized alkyl groups with nucleophilic silicon is reported. Copper catalysis is used to release the silicon nucleophile from Suginome's Si-B reagent. Th
Bench-Stable Stock Solutions of Silicon Grignard Reagents: Application to Iron- and Cobalt-Catalyzed Radical C(sp3)–Si Cross-Coupling Reactions
Xue, Weichao,Shishido, Ryosuke,Oestreich, Martin
supporting information, p. 12141 - 12145 (2018/09/11)
A robust method for the preparation of silicon-based magnesium reagents is reported. The MgBr2 used in the lithium-to-magnesium transmetalation step is generated in situ from 1,2-dibromoethane and elemental magnesium in hot THF. No precipitation of MgBr2 occurs in the heat, and transmetalation at elevated temperature leads to homogeneous stock solutions of the silicon Grignard reagents that are stable and storable in the fridge. This method avoids the preparation of silicon pronucleophiles such as Si?Si and Si?B reagents. The new Grignard reagents were applied to unprecedented iron- and cobalt-catalyzed cross-coupling reactions of unactivated alkyl bromides. The functional-group tolerance of these magnesium reagents is excellent.
Synthesis and reactions of donor cyclopropanes: efficient routes to cis- and trans-tetrahydrofurans
Dunn, Jonathan,Dobbs, Adrian P.
, p. 7386 - 7414 (2015/08/24)
Abstract A detailed study on the synthesis and reactions of silylmethylcyclopropanes is reported. In their simplest form, these donor-only cyclopropanes undergo Lewis acid promoted reaction to give either cis- or trans-tetrahydrofurans, with the selectivity being reaction condition-dependant. The adducts themselves are demonstrated to be an important scaffold for structural diversification. The combination of a silyl-donor group in a donor-acceptor cyclopropane with novel acceptor groups is also discussed.
1,2-HYDROSILYLATION OF DIENES
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Paragraph 000260; 000261, (2014/09/29)
Described herein are platinum complexes of Formula (I) for hydrosilylation of 1,3- dienes. Methods of using the platinum complexes for selective 1,2-hydrosilylation of 1,3- dienes are also provided.
Cyclopropylmethyl- and cyclobutylmethyllithium by an arene-catalyzed lithiation. Stability and reactivity
Pe?afiel, Itziar,Pastor, Isidro M.,Yus, Miguel
experimental part, p. 2928 - 2935 (2010/06/16)
The reaction of (chloromethyl)cyclopropane 5 and (bromomethyl)cyclobutane 8 with lithium and a substoichiometric amount of DTBB, in the presence of different carbonyl compounds as electrophiles, in THF at -78 °C leads, after hydrolysis, to the corresponding cycloalkyl alcohols 6 and 9, respectively. However, when the same starting materials are lithiated using naphthalene as catalyst in diethyl ether and at higher temperature (0 or 25 °C), and then react with the same electrophiles, the final hydrolysis yields the corresponding unsaturated alcohols 7 and 10, respectively.
Regioselective 1,4-silylcupration of 1,3-dienes - Characterization and electrophilic trapping of the intermediate σ-allyl)copper complex
Liepins, Vilnis,Baeckvall, Jan-E.
, p. 3527 - 3535 (2007/10/03)
Silylcupration reactions of 1,3-dienes with a cyanocuprate reagent PhMe2SiCuCNLi produce a (4-silyl-2-alken-1-yl)-copper complex, which was trapped by electrophiles. The use of allylic phosphates as electrophiles resulted in highly regioselecti
Enzymatic synthesis of enantiomerically enriched D- and L-3-silylated alanines by deracemization of DL-5-silylmethylated hydantoins
Smith, Richard J.,Pietzsch, Markus,Waniek, Thomas,Syldatk, Christoph,Bienz, Stefan
, p. 157 - 165 (2007/10/03)
The hydantoinase process was shown to be extendable to the production of highly lipophilic, silicon-containing amino acids. Two hydantoinases of different origin and stereoselectivities and one L-N-carbamoylase were used for the highly stereoselective bioconversion of (dimethyl)phenylsilyl- and 1-methyl-1-silacyclopentyl substituted alanine derivatives. The enantiomeric purities and absolute configuration of the products were determined with reference compounds that were synthesized with the aid of the Evans oxazolidinone auxiliary.
Manganese-Catalyzed Silylmagnesiation of Acetylenes and 1,3-Dienes
Tang, Jun,Shinokubo, Hiroshi,Oshima, Koichiro
, p. 245 - 251 (2007/10/03)
The treatment of 4-benzyloxy-1-butyne with PhMe2SiMgMe in the presence of a catalytic amount of MnCl2 gave a monosilylated product, (E)-PhCH2OCH2CH2CH=CHSiMe2Ph, selectively after an aqueou
