21081-92-5Relevant articles and documents
Generation and Reaction of Samarium(II) Iodide Equivalent from Samarium and Chlorotrimethylsilane/Sodium Iodide System in Acetonitrile
Akane, Noriyuki,Kanagawa, Yoshinori,Nishiyama, Yutaka,Ishii, Yasutaka
, p. 2431 - 2434 (1992)
Samarium(II) iodide equivalent was generated from metallic samarium and Me3SiCl/NaI reagent in acetonitrile under ambient conditions.Dehalogenation of α-halocarbonyl compounds and reductive coupling of ketones were successfully carried out by the use of the samarium(II) species, thus generated, in acetonitrile.
Reductive pinacol coupling of aromatic carbonyl compounds catalytic in chromium(II)
Svato?, Ale?,Boland, Wilhelm
, p. 549 - 551 (2007/10/03)
Reductive coupling of aromatic and heteroaromatic aldehydes and ketones bearing different functional groups to pinacols is effectively catalysed with 1-5 mol % of Cr(II) salts or chromocene in THF/DMF mixtures in the presence of manganese powder and trialkyl chlorosilanes. Excellent dl selectivity can be achieved albeit with lower yield using trialkylsilyl chlorides with bulky substituents.
New Generation Method for a Samarium(II) Equivalent: Me3SiX (X = Br and I)/Sm-Assisted Intermolecular Carbon-Carbon Bond Forming Reactions for Carbonyl Compounds
Akane, Noriyuki,Hatano, Tadashi,Kusui, Hiroko,Nishiyama, Yutaka,Ishii, Yasutaka
, p. 7902 - 7907 (2007/10/02)
Samarium(II) species can be efficiently generated in situ from a reaction between elemental samarium and chlorotrimethylsilane (Me3SiCl)/sodium iodide (NaI) reagent or bromotrimethylsilane (Me3SiBr) in acetonitrile.The reductive coupling reaction of carbonyl compounds was achieved by the action of Sm(II) reagent thus generated from Sm/Me3SiCl/NaI or Sm/Me3SiBr to give the corresponding pinacol products in moderate to high yields.The samarium(II) reagent induced the intermolecular coupling reaction of α,β-unsaturated esters with carbonyl compounds or imines followed by intramolecular cyclization to form the corresponding γ-lactones or γ-lactams in moderate yields.The reaction of α-bromo esters with carbonyl compounds using the Sm(II) species, generated from the Sm/Me3SiX system, led to the corresponding β-hydroxy esters in 52-95percent yields.