1995
DOI: 10.1021/jo00115a020
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A Selective Synthesis of (E)-Vinylsilanes by Cationic Rhodium Complex-Catalyzed Hydrosilylation of 1-Alkynes and Tandem Hydrosilylation/Isomerization Reaction of Propargylic Alcohols to .beta.-Silyl Ketones

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Cited by 115 publications
(44 citation statements)
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“…Column chromatography purifications were carried out by using the flash technique on silica gel 60 (200-400 mesh). 1 H NMR spectroscopy was run by using a Bruker Advance 400 MHz instrument and all spectra were calibrated to d = 7.26 ppm for the signal from the residual proton of the deuterated chloroform solvent; 13 C NMR spectra were calibrated to the middle carbon signal of the triplet for deuterated chloroform (d = 77.00 ppm).…”
Section: Methodsmentioning
confidence: 99%
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“…Column chromatography purifications were carried out by using the flash technique on silica gel 60 (200-400 mesh). 1 H NMR spectroscopy was run by using a Bruker Advance 400 MHz instrument and all spectra were calibrated to d = 7.26 ppm for the signal from the residual proton of the deuterated chloroform solvent; 13 C NMR spectra were calibrated to the middle carbon signal of the triplet for deuterated chloroform (d = 77.00 ppm).…”
Section: Methodsmentioning
confidence: 99%
“…Purification by flash chromatography (20 % dichloromethane in pentane) afforded 94 mg of 3 e (68 % yield including minor isomers). [13] (E)-5-Chloro-1-(triphenylsilyl)-1-pentene (3 f): 5-Chloro-1-pentyne and triphenylsilane were reacted by following the general hydrosilylation procedure and 750 mL of the crude reaction mixture were collected. Purification by flash chromatography (12 % dichloromethane in hexane) afforded 189.7 mg of 3 f (70 % yield including minor isomers).…”
Section: Methodsmentioning
confidence: 99%
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“…The important catalytic activity of platinum supported on carbon, silicates and silica in the hydrosilylation of ethylene, butadiene, acetylene and allyl chloride with trichlorosilane has been reported. 2 There are several examples that have been studied to reach this goal and more expensive catalysts have been employed for this purpose [6][7][8][9] .…”
Section: Introductionmentioning
confidence: 99%
“…and 116c with 0.5 equivalent of (TMS) 3 SiH in the presence of Wilkinson's catalyst 179 efficiently effected the isomerization to give the corresponding (E)-silanes 117a (78%) and 117c (89%). Extended heating (54 h) of 116b in the presence of (TMS) 3 SiH/RhCl(PPh 3 ) 3 /NaI resulted in the quantitative conversion of 116b into 117b.…”
Section: Effect Of Protecting Group: O-acetyl Vs O-toluoylmentioning
confidence: 99%