74120-65-3Relevant articles and documents
Reductive coupling of allylic esters with carbonyl compounds mediated by the mischmetall/[SmI2/Pd0cat.′] cat. system
Medegan, Sedami,Helion, Florence,Namy, Jean-Louis
, p. 4715 - 4722 (2007/10/03)
The mischmetall/[SmI2/Pd0cat.′] cat. system has been used to mediate the allylation of ketones using a variety of allylic esters (acetates, carbonates and phosphates). Thus, a "two-stage catalysis" has been carried out using SmI2 and Pd(PPh3)4 in catalytic amounts together with mischmetall (an alloy of the light lanthanides) as a co-reductant. A catalytic scheme that takes into account previously reported reactions of SmI2/Pd 0cat. and mischmetall/SmI2,Cat. systems is proposed. It has also been shown that palladium complexes catalyse the addition of organolanthanide species to ketones. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Preparation and reactions of samarium diiodide in nitriles
Hamann, Beatrice,Namy, Jean-Louis,Kagan, Henri B.
, p. 14225 - 14234 (2007/10/03)
Samarium diiodide can be prepared from samarium metal in various nitriles. Because of its chemical inertness pivalonitrile is the most suitable solvent. Organic reactions mediated by SmI2 are slower than in THF, but selectivities are often improved. Reactions are greatly accelerated by addition of catalytic amounts of some transition metal salts.
Divalent Lanthanide Derivatives in Organic Synthesis. 1. Mild Preparation of SmI2 and YbI2 and Their Use as Reducing or Coupling Agents
Girard, P.,Namy, J. L.,Kagan, H. B.
, p. 2693 - 2698 (2007/10/02)
The facile synthesis of SmI2 and YbI2 from corresponding metals in THF is described.The reactivity of these potentially powerful reducing agents toward a variety functional groups is tested.Epoxides and sulfoxides are deoxygenated.Aldehydes are selectively reduced in presence of ketones.Alkyl halides or tosylates are converted into alkanes.Only coupling products are obtained from benzylic or allylic halides.In the presence of a SmI2-THF solution, tertiary alcohols are easily obtained from reactions between ketones and alkyl halides.In a similar manner, SmI2 promotes straightforward alkylation of ketones by alkyl sulfonates.Selective addition of polyfunctional halides or tosylates to ketones may be performed.In these reactions, catalytic amounts of FeCl3 enhance the reactivity.