91076-17-4Relevant academic research and scientific papers
Pd-catalyzed cross-coupling of allylsilane-vinylcopper species with aryl and vinyl halides: the first total synthesis of (-)-nomadone
Pulido, Francisco J.,Barbero, Asunción,García, Carlos
experimental part, p. 5535 - 5540 (2009/12/04)
The reaction of allene with a lower order silylcuprate 3 leads to an allylsilane-vinylcopper intermediate 4, which undergoes palladium-catalyzed cross-coupling reaction with both vinyl and aryl halides. The influence of several factors such as the nature
Zinc-catalyzed nucleophilic substitution reaction of chlorosilanes with organomagnesium reagents
Murakami, Kei,Yorimitsu, Hideki,Oshima, Koichiro
experimental part, p. 1415 - 1417 (2009/06/28)
Zinc-catalyzed nucleophilic substitution reactions of chlo-rosilanes with organomagnesium reagents afford various tetraorganosilanes under mild reaction conditions. The reactions can be performed on large scale and allow efficient preparation of functionalized tetraorganosilanes.
Regio- and stereospecific cleavage of silyl- and disilylepoxides with lithium diphenylphosphide
Cuadrado, Purificacion,Gonzalez-Nogal, Ana M.,Sarmentero, M. Angeles
, p. 4491 - 4497 (2007/10/03)
Unsubstituted or α- and β-C-substituted silylepoxides react stereospecifically with lithium diphenylphosphide, optionally followed by methylation, to give vinylphosphonium iodides or vinylphosphine oxides resulting from α-opening and silyl enol ethers, vi
Silyl-cupration of a propargylsilane as a test for the reversibility of a metallo-metallation
De Dios, Maria Angeles Cubillo,Fleming, Ian,Friedhoff, Wibke,Woode, Philip D.W.
, p. 69 - 72 (2007/10/03)
Silyl-cupration of propargylsilanes is normal in giving mainly the product with a silyl group at the terminus and the copper atom in the centre. There is no evidence of the copper atom and the originally-resident silyl group undergoing a retro silyl-cupration to give an allenylsilane.
New findings on the regiochemistry of the silylcupration of allene
Blanco,Blanco, Francisco J.,Cuadrado,Cuadrado, Purificacion,Gonzalez,Gonzalez, Ana M.,Pulido,Pulido, Francisco J.,Fleming,Fleming, Ian
, p. 8881 - 8882 (2007/10/02)
Allene 1 reacts at -40*C with the phenyldimethylsilylcopper reagent 6, with the opposite regioselectivity to that shown by the corresponding silylcuprate reagent 2, to give allylsilanes 7 and 10-15 rather than vinylsilanes.
A 1,2-Silicon Shift in Cyclopropylidenes leading to 1-Trialkylsilylcyclopropenes
Baird, Mark S.,Dale, Cynthia M.,Dulayymi, Juma'a R. Al
, p. 1373 - 1374 (2007/10/02)
1,1-Dibromo-2-trialkylsilylcyclopropanes, readily prepared by dibromocyclopropanation of vinyltrialkylsilanes, react with methyllithium at -90 to 20 deg C to give high yields of trialkylsilylcyclopropenes in which the silicon has apparently migrated to C-1.
The Reaction of tert-Butyldiphenylsilylcuprates with Allenes
Barbero, Asuncion,Cuadrado, Purificacion,Gonzalez, Ana M.,Pulido, Francisco J.,Fleming, Ian
, p. 2811 - 2816 (2007/10/02)
Bis(tert-butyldiphenylsilyl)cuprate 1 reacts with allenes to form allyl- and vinyl-silanes.With allene itself the cuprate reagent shows a different regiochemistry from that of bis(phenyldimethylsilyl)cuprate.The regiochemistry can be controlled by choosing an appropriate reaction temperature.The intermediate cuprate 4 resulting from the addition of 1 to allene reacts with a wide variety of electrophiles giving functionalised allylsilanes.Phenylallenes isomerise to acetylenes.
THE SILYL-CUPRATION AND STANNYL-CUPRATION OF ALLENES
Fleming, Ian,Rowley, Michael,Cuadrado, Purificacion,Gonzalez-Nogal, Ana M.,Pulido, Francisco J.
, p. 413 - 424 (2007/10/02)
The stoichiometric silyl-cupration of allene 7, followed directly by treating the intermediate cuprate with a proton, with a range of carbon electrophiles, and with chlorine gives the vinylsilanes 8-13.Alternatively, when iodine is the electrophile, the product is the vinyl iodide 16.This can then be metallated and treated with a proton or a range of carbon electrophiles to give the allylsilanes 18-21.More-substituted allenes also undergo silyl-cupration followed by protonation, phenylallenes giving vinylsilanes, and alkylallenes giving, on the whole, allylsilanes.Stoichiometric stannyl-cupration of allenes takes place, with similar but less reliable regiocontrol to that of the corresponding silyl-cupration.
The Syntheses of Allylsilanes and Vinylsilanes by Silyl-cupration of Allenes
Fleming, Ian,Pulido, Francisco J.
, p. 1010 - 1011 (2007/10/02)
Allenes react with silyl-cuprate reagents to give either allylsilanes or vinylsilanes, depending upon the substituents on the allene.
TRANSITION-METAL CATALYZED SILYLMETALATION OF ALLENES
Morizawa, Yoshitomi,Oda, Hiroji,Oshima, Koichiro,Nozaki, Hitosi
, p. 1163 - 1166 (2007/10/02)
Addition of PhMe2SiMgMe, (PhMe2Si)2Zn, or PhMe2SiAlEt2 to allenes proceeds in the presence of various transition-metal catalysts.Whereas copper catalyzed silylmagnesation of 1,2-cyclononadiene gives 1-dimethyl-phenylsilyl-1-cyclononene exclusively, palladium catalyzed silylalumination affords 3-dimethylphenylsilyl-1-cyclononene preferentially with high degrees of regioselectivity.
