111133-19-8Relevant academic research and scientific papers
Preparation of allylsilanes via cross-metathesis
Crowe, William E.,Goldberg, Daniel R.,Zhang, Zhijia J.
, p. 2117 - 2120 (1996)
Allylsilanes are prepared by simple metathetical cross-coupling of terminal olefins with allyltrimethylsilane. Allyltrimethylsilane coupling with π-substituted terminal olefins (styrenes, 1-phenyl-1,3-butadiene, and acrylonitrile) proceeds in excellent yi
Palladium-Catalyzed Silylation of Allylic Acetates with Hexamethyldisilane or (Trimethylsilyl)tributylstannane
Tsuji, Yasushi,Kajita, Satoshi,Isobe, Shinya,Funato, Masahiro
, p. 3607 - 3608 (1993)
Various allylic acetates (1a-j) are silylated with hexamethyldisilane (Me3SiSiMe3, 2) in the presence of a catalytic amount of Pd(DBA)2 and LiCl at 100 deg C to afford the corresponding allylic silanes in high yields.In addition, (trimethylsilyl)tributylstannane (Me3SiSnBu3, 3) can be used for the silylation of aromatic allylic acetates 1g-j at room temperature.
Stereospecific Iron-Catalyzed Carbon(sp2)-Carbon(sp3) Cross-Coupling with Alkyllithium and Alkenyl Iodides
Lu, Xiao-Lin,Shannon, Mark,Peng, Xiao-Shui,Wong, Henry N. C.
supporting information, p. 2546 - 2549 (2019/03/26)
An efficient synthetic protocol involving iron-catalyzed cross-coupling reactions between organolithium compounds and alkenyl iodides as key coupling partners was achieved. More than 30 examples were obtained with moderate to good yields and high stereospecificity. Gram-scale and synthetic applications of this procedure are recorded herein to demonstrate its feasibility and potential utilization.
An efficient palladium catalyzed Mizoroki-Heck cross-coupling in water
Jadhav, Sanjay N.,Rode, Chandrashekhar V.
supporting information, p. 5958 - 5970 (2017/12/26)
The homogeneous Pd-catalysed Mizoroki-Heck coupling reaction was successfully performed in water in the absence of any additives under aerobic conditions. The various key reaction parameters that affect the yield of the desired cross-coupling product were optimized. The Pd(PPh3)4/Et3N/H2O/98 °C catalyst system was found to be highly active (TOF = 12 to 14 h-1) towards achieving excellent yield of the Mizoroki-Heck coupling products for a wide range of electron-withdrawing as well as electron-donating aryl bromides and chlorides in the shortest reaction time. Pd(PPh3)4 catalyst deactivation during the Mizoroki-Heck coupling reaction was investigated and to evolve a strategy for achieving ten times Pd-metal recyclability without appreciable loss of its activity. Thus, the proposed mechanism provides access to a variety of olefins in aqueous medium, making this protocol eco-friendly.
Cobalt-catalyzed mono-coupling of R3SiCH2MgCl with 1,2-dihalogenoethylene: A general route to γ-substituted (E)-allylsilanes
Kamachi, Taku,Kuno, Akiko,Matsuno, Chikashi,Okamoto, Sentaro
, p. 4677 - 4679 (2007/10/03)
The reaction of trimethylsilylmethylmagnesium chloride (TMSCH 2MgCl) with 1,2-dihalogenoethylene in the presence of 1mol% of Co(II) or Co(III) acetylacetonate in THF or THF-NMP proceeded exclusively in a mono-coupling pathway to provide 3-trimethylsilyl-1-halogeno-1-propene with >99% of E geometry in high yield, which was converted to a variety of γ-substituted allylsilanes by Ni- or Pd-catalyzed coupling with organometallic compounds.
REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALLYLTRIMETHYLSILANES VIA KRIEF-REICH ELIMINATION IN β-SELENO-γ-SILYL ALCOHOLS
Sarkar, Tarun K.,Ghosh, Sunil K.,Satapathi, Tushar K.
, p. 1885 - 1898 (2007/10/02)
The synthesis of (E)-allyltrimethylsilanes by regio- and stereocontrolled pathways is described based on the preference for Krief-Reich elimination over silicon-controlled rearrangement in β-seleno-γ-silyl alcohols, readily available from α-selenoaldehydes, 10 - 12.Usefulness of this protocol for the introduction of the allylsilane function α to the carbonyl group in cycloalkanones as well as for the preparation of unsymmetrically substituted allylsilanes is also reported.
