156191-12-7Relevant academic research and scientific papers
Iron(III) fluorinated porphyrins: Greener chemistry from synthesis to oxidative catalysis reactions
Rebelo, Susana L. H.,Silva, Andre M. N.,Medforth, Craig J.,Freire, Cristina
, (2016)
: Iron(III) fluorinated porphyrins play a central role in the biomimetics of heme enzymes and enable cleaner routes to the oxidation of organic compounds. The present work reports significant improvements in the eco-compatibility of the synthesis of 5,10,15,20-tetrakis-pentafluorophenylporphyrin (H2 TPFPP) and the corresponding iron complex [Fe(TPFPP)Cl], and the use of [Fe(TPFPP)Cl] as an oxidation catalyst in green conditions. The preparations of H2 TPFPP and [Fe(TPFPP)Cl] typically use toxic solvents and can be made significantly greener and simpler using microwave heating and optimization of the reaction conditions. In the optimized procedure it was possible to eliminate nitrobenzene from the porphyrin synthesis and replace DMF by acetonitrile in the metalation reaction, concomitant with a significant reduction of reaction time and simplification of the purification procedure. The Fe(III)porphyrin is then tested as catalyst in the selective oxidation of aromatics at room temperature using a green oxidant (hydrogen peroxide) and green solvent (ethanol). Efficient epoxidation of indene and selective oxidation of 3,5-dimethylphenol and naphthalene to the corresponding quinones is observed.
Microwave-assisted silylation of graphite oxide and iron(III) porphyrin intercalation
Lipińska, Monika E.,Novais, Jo?o P.,Rebelo, Susana L.H.,Bachiller-Baeza, Belén,Rodríguez-Ramos, Inmaculada,Guerrero-Ruiz, Antonio,Freire, Cristina
, p. 475 - 484 (2014)
The hybrid material graphite oxide (GO) intercalated with an iron(III) porphyrin was obtained upon a silylation reaction of GO with 3-bromotrimethoxypropylsilane (BrTMS) followed by metalloporphyrin immobilization. Diverse reaction conditions and microwav
Indigo dye production by enzymatic mimicking based on an iron(III)porphyrin
Rebelo, Susana L.H.,Linhares, Margarida,Simoes, Mario M.Q.,Silva, Artur M.S.,Neves, M. Graca P.M.S.,Cavaleiro, Jose A.S.,Freire, Cristina
, p. 33 - 40 (2014/06/09)
A novel indigo synthesis is based on a simple and cost-effective model system of the enzymes involved in the natural and biocatalytic productions. The method considers the oxidation of indole by hydrogen peroxide, being catalyzed by an iron(III)porphyrin in ethanol, as solvent, and no other additives. The yields of indigo and of the other oxidized indolinoid derivatives were found to be dependent on the metalloporphyrin system used and on the control of the oxidation conditions. Significant reductions of the environmental impact relatively to the present industrial production and of the costs relatively to the biocatalytic methodologies were obtained. The enhanced indigo production in the presence of the iron(III)porphyrin-ethanol catalytic system relatively to the manganese(III)porphyrin-acetonitrile system can be rationalized by the formation of different active species in the two systems.
Catalysed anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant
Du, Yi-Dan,Tse, Chun-Wai,Xu, Zhen-Jiang,Liu, Yungen,Che, Chi-Ming
supporting information, p. 12669 - 12672 (2015/05/20)
Anti-Markovnikov oxidation of terminal aryl alkenes to aldehydes and transformation of N-methyl aryl tertiary amines to formamides with H2O2 as a terminal oxidant under mild conditions have been achieved with moderate to good product yields using [FeIII(TF4DMAP)OTf] as catalyst. This journal is
