72157-48-3Relevant academic research and scientific papers
Iron-catalyzed stereospecific activation of olefinic C-H bonds with grignard reagent for synthesis of substituted olefins
Ilies, Laurean,Asako, Sobi,Nakamura, Eiichi
supporting information; experimental part, p. 7672 - 7675 (2011/06/26)
The reaction of an aryl Grignard reagent with a cyclic or acyclic olefin possessing a directing group such as pyridine or imine results in the stereospecific substitution of the olefinic C-H bond syn to the directing group. The reaction takes place smoothly and without isomerization of the product olefin in the presence of a mild oxidant (1,2-dichloro-2-methylpropane) and an aromatic cosolvent. Several lines of evidence suggest that the reaction proceeds via iron-catalyzed olefinic C-H bond activation rather than an oxidative Mizoroki-Heck-type reaction.
Palladium-Catalyzed Cross-Coupling of β-(Methanesulfonyl)oxy Enones with Organostannanes
Hettrick, Christina M.,Kling, James K.,Scott, William J.
, p. 1489 - 1492 (2007/10/02)
β-(Methanesulfonyl)oxy enones, derived from 1,3-diones, cross-couple with vinylstannanes in 50-80percent yields when a substoichiometric amount of Pd(PPh3)4 and stoichiometric lithium bromide are used.Phenyltributylstannane affords low yields of cross-coupled product.Tetrabutyltin, tributyltin hydride, and ethynyltributyltin do not couple under the reaction conditions.The reaction is proposed to involve in situ formation of the β-bromo enone, oxidative addition to the Pd(0) catalyst, transmetalation, and reductive elimination to afford cross-coupled products.The analogous enol phosphates undergo coupling in low yields, the major product resulting from regeneration of the 1,3-dione.
