255041-56-6Relevant articles and documents
Ruthenium-catalyzed regiospecific borylation of methyl C-H bonds
Murphy, Jaclyn M.,Lawrence, Joshua D.,Kawamura, Kazumori,Incarvito, Christopher,Hartwig, John F.
, p. 13684 - 13685 (2007/10/03)
We report the regiospecific, ruthenium-catalyzed borylation of saturated terminal C-H bonds. Alkylboronates were obtained in 78-98% yields. The borylations of alkanes, trialkylamines, protected alcohols, and fluoroalkanes occurred regiospecifically at the methyl group that is least sterically hindered. In contrast to most organometallic C-H activation, the reactions of alkanes occurred in higher yields than the reactions of arenes. Reactions were conducted that probed steric and electronic effects on the alkyl borylation. These reactions showed that the borylation occurred preferentially at the methyl group that is least sterically hindered and most electron-deficient. Ruthenium compounds containing boryl ligands were synthesized, and one was characterized by X-ray crystallography. One of these compounds contained a rare bridging boryl ligand and served as a catalyst precursor for the borylation of octane. Copyright
Catalytic, regiospecific end-functionalization of alkanes: Rhenium-catalyzed borylation under photochemical conditions
Chen, Huiyuan,Hartwig, John F.
, p. 3391 - 3393 (2007/10/03)
Approaching a Holy Grail? A regioselective functionalization of alkanes occurs with commercially available rhenium catalysts and borane reagents under photochemical conditions [Eq.(1)]. Mechanistic studies indicate that the regioselectivity results from a direct thermal reaction of a photochemically generated 16- electron boryl complex with alkane.
