54380-53-9Relevant academic research and scientific papers
Use of cyclohexa-2,5-dien-1-yl-silanes as precursors for gaseous hydrosilanes
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Paragraph 0026 - 0028, (2015/03/18)
The invention relates to the use of cyclohexa-2,5-dien-1-yl-silanes of general formula I for generation of hydrosilanes in solution using a strong Lewis acid. This way, e.g., alkenes can be hydrosilylated in good yields using the cyclohexa-2,5-dien-1-yl-silanes of general formula I as transfer hydrosilylating agents in the presence of a strong Lewis acid as catalyst with concomitant formation of an arene solvent.
USE OF CYCLOHEXA-2,5-DIEN-1-YL-SILANES AS PRECURSORS FOR GASEOUS HYDROSILANES
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Page/Page column 8; 9, (2015/03/28)
The invention relates to the use of cyclohexa-2,5-dien-1 -yl-silanes of general formula (I), for generation of hydrosilanes in solution using a strong Lewis acid. This way, e.g., alkenes or carbonyl compounds can be hydrosilylated in good yields using the cyclohexa-2,5-dien-1 - yl-silanes of general formula I as transfer hydros! lylating agents in the presence of a strong Lewis acid as catalyst with concomitant formation of an arene solvent.
3-silylated cyclohexa-1,4-dienes as precursors for gaseous hydrosilanes: The B(C6F5)3-catalyzed transfer hydrosilylation of alkenes
Simonneau, Antoine,Oestreich, Martin
supporting information, p. 11905 - 11907 (2013/11/19)
Set Me3SiH free! The strong Lewis acid B(C6F 5)3 catalyzes the release of hydrosilanes from 3-silylated cyclohexa-1,4-dienes with concomitant formation of benzene. Subsequent B(C 6F5)3
Fluorination process
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Page/Page column 20, (2008/06/13)
Compounds of formula (II), (IIIa) or (IIIb) (variables are described in the specification) are prepared by fluorination of β,γ-unsaturated alkyl silanes. These compounds are useful as building blocks in the pharmaceutical industry.
Sequential desymmetrization-fluorination: Enantioselective synthesis of fluorinated cyclitols
Purser, Sophie,Odell, Barbara,Claridge, Timothy D.W.,Moore, Peter R.,Gouverneur, Veronique
, p. 9176 - 9185 (2007/10/03)
An asymmetric synthesis of enantioenriched, highly functionalized fluorinated carbocycles has been developed based on an enantioselective Sharpless dihydroxylation of cyclohexa-dienylsilanes, combined with a diastereoselective electrophilic fluorodesilyla
Stereoselective synthesis of (+)-nephrosteranic acid, (+)-trans-cognac lactone, and (+)-trans-whisky lactone using a chiral cyclohexadienyl Ti compound
Schleth, Florian,Vogler, Thomas,Harms, Klaus,Studer, Armido
, p. 4171 - 4185 (2007/10/03)
We present the stereoselective transfer of cyclohexadienyl from 3-metalated 1,4-cyclohexadienes to various aldehydes. Lewis-acid-mediated "allylation" of aldehydes by treatment with 3-silylated and 3-stannylated 1,4-cyclohexadienes could not be achieved with high diastereoselectivity. In contrast, cyclohexadienyl titanium compounds reacted with both aliphatic and aromatic aldehydes with good-to-excellent diastereoselectivities. Reaction of a chiral TADDOL-derived (TADDOL, 2,2-dimethyl-α,α,α′,α′-tetraphenyl-1, 3-dioxolandimethanol) cyclohexadienyl Ti derivative with various aldehydes led to the corresponding homoallylic alcohols with excellent diastereo- and enantioselectivities. Lower selectivities were obtained with chiral β-cyclohexadienyldiisopinocampheylborane. The 1,3-cyclohexadienes are very useful building blocks for the preparation of biologically important γ-butyrolactones. Short efficient syntheses of (+)-nephrosteranic acid, (+)-trans-whisky lactone, and (+)-iram-cognac lactone by desymmetrization of 1,4-cyclohexadiene are described.
Silylated cyclohexadienes as new radical chain reducing reagents: Preparative and mechanistic aspects
Studer, Armido,Amrein, Stephan,Schleth, Florian,Schulte, Tobias,Walton, John C.
, p. 5726 - 5733 (2007/10/03)
Various silylated 1,4-cyclohexadienes are presented as superior tin hydride substitutes for the conduction of various radical chain reductions. Debrominations, deiodinations, and deselenations can be performed using these environmentally benign reagents. Furthermore, Barton - McCombie-type deoxygenations using silylated cyclohexadienes are described. Radical cyclizations, ring expansions, and Giesetype addition reactions with the new tin hydride substitutes are presented. The polymerization of styrene can be regulated using silylated cyclohexadienes. Rate constants for hydrogen atom abstraction from two 1-silyl-cyclohexadienes by primary C-radicals were determined. The effects of the cyclohexadiene substituents on the reaction outcomes are discussed. Finally, qualitative EPR experiments on silyl radical expulsion from silylated cyclohexadienyl radicals are presented.
Desymmetrization of cyclohexa-1,4-dienes - A straightforward route to cyclic and acyclic polyhydroxylated systems
Landais, Yannick,Zekri, Elisabeth
, p. 4037 - 4053 (2007/10/03)
A straightforward route to polyols, amino polyols, polysubstituted lactols and lactones from readily available arenes has been devised. It uses a three- or four-step sequence involving a Birch reduction of the arene, followed by desymmetrization through d
Desymmetrization of Cyclohexadienylsilanes. Regio-, Diastereo-, and Enantioselective Access to Sugar Mimics
Angelaud, Remy,Babot, Odile,Charvat, Trevor,Landais, Yannick
, p. 9613 - 9624 (2007/10/03)
Desymmetrization of cyclohexadienylsilanes available from Birch reduction of the corresponding arylsilanes is efficiently carried out using Sharpless asymmetric dihydroxylation and aminohydroxylation. Complete diastereocontrol and reasonable enantiocontrol have been attained during the preparation of the desired diols. An excellent regiocontrol has also been observed during aminohydroxylation of dienylsilanol 6b. The resulting diol 8 and hydroxycarbamate 27 have then been elaborated further, offering a straightforward access to various types of cyclitols, aminocyclitols, carbasugars, as well as the antibiotic palitantine 4. The complete functionalization of the original arylsilanes 5 is thus typically achieved in fewer than eight steps with high stereoselectivities and excellent overall yield.
