Abstract:Iron nanoparticles prepared by reducing FeCl(3) with three equivalents of EtMgCl in THF are effective catalysts for the hydrogenation of alkenes and alkynes under moderate conditions.
“…Fe I , [9,10] Fe 0 , [10,11] and Fe ÀII [12] species have been reported. In contrast, no deuterated product was detected when the reaction was carried out with NaBH 4 in CD 3 CN.…”
mentioning
confidence: 98%
“…[3][4][5] Hydrides of other main-group elements including silicon, [3a] boron, [3c, 4e-h] gallium, [4b] and indium [4a-d] as well as hydrides of transition metals have been examined. [8] Iron is known to accommodate low oxidation states, [9][10][11][12] and thus we decided to investigate iron(II) catalysts in the presence of NaBH 4 for the direct reduction and cyclization of organic halides. Iron is abundant, cheap, and has low toxicity.…”
Iron made'em: iron(II) complexes such as FeCl(2) and [FeCl(2)(dppe)(2) ] (dppe=1,2-bisdiphenylphosphinoethane) are efficient precatalysts for the radical cyclization of unsaturated iodides and bromides in the presence of NaBH(4). Cyclic voltammetry studies suggests that the reaction occurs through a radical mechanism via an anionic hydrido iron(I) species as the key intermediate for the activation of the substrates by electron transfer.
“…Fe I , [9,10] Fe 0 , [10,11] and Fe ÀII [12] species have been reported. In contrast, no deuterated product was detected when the reaction was carried out with NaBH 4 in CD 3 CN.…”
mentioning
confidence: 98%
“…[3][4][5] Hydrides of other main-group elements including silicon, [3a] boron, [3c, 4e-h] gallium, [4b] and indium [4a-d] as well as hydrides of transition metals have been examined. [8] Iron is known to accommodate low oxidation states, [9][10][11][12] and thus we decided to investigate iron(II) catalysts in the presence of NaBH 4 for the direct reduction and cyclization of organic halides. Iron is abundant, cheap, and has low toxicity.…”
Iron made'em: iron(II) complexes such as FeCl(2) and [FeCl(2)(dppe)(2) ] (dppe=1,2-bisdiphenylphosphinoethane) are efficient precatalysts for the radical cyclization of unsaturated iodides and bromides in the presence of NaBH(4). Cyclic voltammetry studies suggests that the reaction occurs through a radical mechanism via an anionic hydrido iron(I) species as the key intermediate for the activation of the substrates by electron transfer.
“…The terminal iron-catalyzed hydrogenation can be viewed as a non-toxic alternative to protocols employing Raney nickel catalysts. [24] Hydrogenation of both allylbenzene derivatives was complete within 4 h at 1 bar H 2 and room temperature; conversion of the minor 2-(1-propenyl)anisole components was somewhat slower (20 h). Further results toward this end will be communicated in due course.…”
An operationally simple iron-catalyzed reductive cross-coupling reaction between aryl halides and allyl electrophiles has been developed. The underlying domino process exhibits high versatility with respect to the allylic leaving group (acetate, tosylate, diethyl phosphate, methyl carbonate, trimethylsilanolate, methanethiolate, chloride, bromide) and high economic and environmental sustainability with respect to the catalyst system (0.2-5 mol% tris(acetylacetonato)ironA C H T U N G T R E N N U N G (III), ligand-free) and reaction conditions (tetrahydrofuran, 0 8C, 45 min).
“…This activity in the hydrogenation of alkenes to alkanes agrees well with the behavior usually observed in the batch hydrogenation of alkynes, where olefins (primary products) get consumed as soon as there is no more alkyne in the reaction mixture. 9,41 It is worth noting that no PHIP effects were observed in the hydrogenation of 1-butene on Cu/SiO 2-700 (Fig. S5†).…”
Mechanistic insight into the semihydrogenation of 1-butyne and 2-butyne on Cu nanoparticles supported on partially dehydroxylated silica (Cu/SiO2-700) was obtained using parahydrogen.
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