215728-76-0Relevant articles and documents
Catalytic Barbier-type reactions of lactones and esters mediated by the Mischmetall/SmI2(cat.) system or the Mischmetall/[SmI2/NiI2(cat'.)](cat.) system
Lannou, Marie-Isabelle,Hélion, Florence,Namy, Jean-Louis
, p. 8007 - 8010 (2007/10/03)
Barbier-type reactions using SmI2 in catalytic amounts together with Mischmetall as a coreductant, involving lactones or esters and a variety of organic halides (allylic, benzylic and alkyl), have been performed. With alkyl halides and five- or six-membered ring lactones, catalytic quantities of nickel diiodide (with respect to SmI2) must be added to achieve reactions. Thus, a 'two-stage catalysis' is carried out. Unexpectedly, it was found that with esters or an unstrained lactone the Mischmetall/SmI2 (catalytic) system is more reactive than samarium diiodide in stoichiometric amounts. Tentative interpretations of the catalytic role of NiI2 are proposed.
Organolithium reagents from alkyl phenyl ethers
Bachki, Abderrazak,Foubelo, Francisco,Yus, Miguel
, p. 7759 - 7762 (2007/10/03)
The reaction of primary alkyl or vinyl phenyl ethers (1) as well as 2,3- dihydrobenzofuran (3) with an excess of lithium powder and a catalytic amount of DTBB (5 %) in THF at room temperature leads to the corresponding organolithium intermediates, which by treatment with different electrophiles [H2O, D2O, Me3SiCl, Bu(t)CHO, PhCHO, Me2CO, Et2CO, (CH2)4CO, (CH2)5CO, PhCOMe] and final hydrolysis affords the expected products 2 and 4.