167865-53-4Relevant academic research and scientific papers
Copper-Catalyzed Cross-Coupling of Vinyliodonium Salts and Zinc-Based Silicon Nucleophiles
Zhang, Liangliang,Oestreich, Martin
supporting information, p. 8061 - 8063 (2019/01/14)
A silylation of vinyliodonium salts using zinc-based silicon reagents as nucleophiles is reported. This cross-coupling is catalyzed by copper, and vinylsilanes are obtained in high yield likely following a Cu(I)/Cu(III) reaction mechanism. The procedure i
Some synthetic applications of vinylphosphane oxides
Gonzalez-Nogal, Ana M.,Cuadrado, Purificacion,Sarmentero, Maria A.
experimental part, p. 9610 - 9619 (2011/01/03)
Vinylphosphane oxides have been used as Michael acceptors for the diastereoselective synthesis of anti α-functionalized-β-silylated phosphane oxides and β-stannyl-, β-phenylthio- or β-phosphanyl phosphane oxides. Although the utility of these substrates as dipolarophiles was more limited, we have obtained a mixture of 3- and 4-phosphanylpyrazoles in which the latter is the major regioisomer, by 1,3-cycloaddition with N-phenylsydnone. Moreover, vinylphosphane oxides reacted with aldehydes in the presence of LDA by a Baylis-Hillman type reaction, leading to (E)-β-hydroxyphosphane oxides, which were readily converted in allenes. It is noteworthy that the application of this methodology to silylated substrates has permitted us to synthesize an interesting and more versatile silylallene.
Silylzincation of carbon-carbon multiple bonds revisited
Auer, Gertrud,Oestreich, Martin
, p. 311 - 313 (2008/02/08)
The first investigation of the copper-catalyzed silylzincation of alkynes as well as a diene and styrene using bis(triorganosilyl) zinc reagents led to the development of an efficient procedure and the disclosure of an unexpected bissilylation and unfores
The Peterson olefination using the tert-butyldiphenylsilyl group: Stereoselective synthesis of di- and trisubstituted alkenes
Barbero,Blanco,Garcia,Pulido
, p. 1223 - 1228 (2007/10/03)
The reaction of α-tert-butyldiphenylsilyl carbonyl compounds with organometallics leads with a high diastereoselectivity to erythro-β-hydroxysilanes, which under acidic or basic elimination conditions give E or Z di- and trisubstituted alkenes.
Synthesis of vinylsilanes by silyl-cupration of acetylenes using tert-butyldiphenylsilyl-cuprate reagents
Barbero, Asuncion,Cuadrado, Purificacion,Fleming, Ian,Gonzalez, Ana M.,Pulido, Francisco,Sanchez, Alicia
, p. 1525 - 1532 (2007/10/02)
The tert-butyldiphenylsilyl-cuprate 2 reacts with acetylenes 1 and 5-10 to give vinyl-cuprates 3 and 11, which react with electrophiles to give the vinylsilanes 4 and 12-17 carrying the relatively hindered and hence unreactive tert-butyldiphenylsilyl group.In comparative tests, the tert-butyldiphenylsilyl group shows some properties that are usefully different from those of relatively unhindered silyl groups and others that are similar.
