10519-88-7Relevant articles and documents
Andrianov et al.
, (1972)
Zinc mediated allylations of chlorosilanes promoted by ultrasound: Synthesis of novel constrained sila amino acids
Ramesh, Remya,Reddy, D. Srinivasa
supporting information, p. 4093 - 4097 (2014/06/10)
A simple, fast and efficient method for allylation and propargylation of chlorosilanes through zinc mediation and ultrasound promotion is reported. As a direct application of the resulting bis-allylsilanes, three novel, constrained sila amino acids are prepared for the first time. The design and synthesis of the constrained sila analogue of GABA (γ-amino butyric acid) is a highlight of this work. This journal is the Partner Organisations 2014.
Controlled introduction of allylic group to chlorosilanes
Li, Zhifang,Cao, Xiaojun,Lai, Guoqiao,Liu, Jinhua,Ni, Yong,Wu, Jirong,Qiu, Huayu
, p. 4740 - 4746 (2007/10/03)
Allylation of chlorosilanes has been achieved with allylsamarium bromide, especially in a controlled manner. Thus allylation of trisubstituted chlorosilanes (R3SiCl) afforded a variety of aryl, aralkyl, and alkenyl substituted allylsilanes. Dichlorosilanes (R2SiCl2) can either afford monoallylated silanes or diallylated silanes depending on the amount of allylsamarium bromide used. Similarly, trichlorosilanes (RSiCl3) can selectively afford mono-, di-, and tri-allylation products. Finally, perchlorosilane (SiCl4) was allylated stepwise and the corresponding silanes containing one, two, three or four allylic groups, respectively, were obtained in satisfactory yields.
Cross-coupling of triallyl(aryl)silanes with aryl bromides and chlorides: An alternative convenient biaryl synthesis
Sahoo, Akhila K.,Oda, Takuro,Nakao, Yoshiaki,Hiyama, Tamejiro
, p. 1715 - 1727 (2007/10/03)
Cross-coupling of a diverse range of aryl bromides with triallyl(aryl)silanes is effective in the presence of PdCl2/PCy 3 and tetrabutylammonium fluoride (TBAF) in DMSO-H2O to give various biaryls in good yields. It is worthwhile to note that the all-carbon-substituted arylsilanes, stable towards moisture, acid, and base and easily accessible, serve as a highly practical alternative to their aryl(halo)silane counterparts. A catalyst system consisting of [η3-C3H5)PdCl]2 and 2-[2,4,6-(i-Pr)3C6Ha]-C6H4PCy 2 and use of TBAF· 3 H2O in THF-H2O are effective especially for the cross-coupling with aryl chlorides. Both of the catalyst systems tolerate a broad spectrum of common functional groups. The high efficiency of reactions is presumably due to the ready cleavage of the allyl groups upon treatment with TBAF·3 H2O and an appropriate amount of water. Diallyl(diphenyl)silane also cross-couples with various aryl bromides and chlorides in good yields, whereas allyl(triphenyl)silane gives the cross-coupled products in only moderate yields. Through sequential cross-coupling of bromochlorobenzenes with different arylsilanes, a range of unsymmetrical terphenyls are accessible in good overall yields.
