1502-24-5Relevant articles and documents
Stereoselective alkane hydroxylations by metal salts and m-chloroperbenzoic acid
Nam, Wonwoo,Ryu, Ju Yeon,Kim, Inwoo,Kim, Cheal
, p. 5487 - 5490 (2002)
Simple metal (M=Mn, Fe, Co) perchlorates associated with m-chloroperbenzoic acid are able to conduct stereoselective alkane hydroxylations via a mechanism involving metal-based oxidants; the catalytic activity of the metal salts is in the order of Co(ClO4)2>Mn(ClO4)2>Fe (ClO4)2.
Stereospecific Alkane Hydroxylation with H2O2 Catalyzed by an Iron(II)-Tris(2-pyridylmethyl)amine Complex
Kim, Cheal,Chen, Kui,Kim, Jinheung,Que, Lawrence
, p. 5964 - 5965 (1997)
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Stereoselective oxidation of alkanes with: M -CPBA as an oxidant and cobalt complex with isoindole-based ligands as catalysts
Nesterova, Oksana V.,Kopylovich, Maximilian N.,Nesterov, Dmytro S.
, p. 93756 - 93767 (2016/10/21)
Two complexes with isoindole-core ligands of general formula [M{C6H4C(NH2)NC(ONCMe2)2}2](NO3)2 (M = Co for 1 and M = Ni for 2) were studied as catalysts for the mild stereoselective alkane oxidation with m-chloroperbenzoic acid (m-CPBA) as an oxidant and cis-1,2-dimethylcyclohexane (cis-1,2-DMCH) as a main model substrate. Complex 1 disclosed a pronounced activity, with high retention of stereoconfiguration of substrates (>98% for cis-1,2-DMCH) and highest cis/trans ratio of tertiary alcohols (products) of 56, under mild conditions. The best achieved yields of tertiary cis-alcohols were of 13.7 and 50.5%, based on the substrate (cis-1,2-DMCH) and the oxidant (m-CPBA) respectively. Kinetic experiments, high bond and stereoselectivity parameters, kinetic isotope effect of 7.2(2) in the oxidation of cyclohexane, and incorporation of 18O from H218O support the involvement of CoIVO high-valent metal-oxo intermediates as main C-H attacking species.
Catalytic oxidation of alkanes by a (salen)osmium(VI) nitrido complex using H2O2 as the terminal oxidant
Chen, Man,Pan, Yi,Kwong, Hoi-Ki,Zeng, Raymond J.,Lau, Kai-Chung,Lau, Tai-Chu
supporting information, p. 13686 - 13689 (2015/09/02)
The osmium(vi) nitrido complex, [OsVI(N)(L)(CH3OH)]+ (1, L = N,N′-bis(salicylidene)-o-cyclohexyldiamine dianion) is an efficient catalyst for the oxidation of alkanes under ambient conditions using H2O2 as the oxidant. Alkanes are oxidized to the corresponding alcohols and ketones, with yields up to 75% and turnover numbers up to 2230. Experimental and computational studies are consistent with a mechanism that involves O-atom transfer from H2O2 to [OsVI(N)(L)]+ to generate an [OsVIII(N)(O)(L)]+ active intermediate.
Catalytic oxidation of alkanes by iron bispidine complexes and dioxygen: Oxygen activation versus autoxidation
Comba, Peter,Lee, Yong-Min,Nam, Wonwoo,Waleska, Arkadius
supporting information, p. 412 - 414 (2014/01/06)
Organic substrates (specifically cis-1,2-dimethylcyclohexane, DMCH) are oxidized by O2 in the presence of iron(ii)-bispidine complexes. It is shown that this oxidation reaction is not based on O2 activation by the nonheme iron catalysts as in Nature but due to a radical-based initiation, followed by a radical- and ferryl-based catalytic reaction.