Insight into the chemoselective aromaticvs.side-chain hydroxylation of alkylaromatics with H2O2catalyzed by a non-heme imine-based iron complex

Ticconi, Barbara; Capocasa, Giorgio; Cerrato, Andrea; Stefano, Stefano Di; Lapi, Andrea; Marincioni, Beatrice; Olivo, Giorgio; Lanzalunga, Osvaldo

doi:10.1039/d0cy01868f

Cited by 7 publications

(10 citation statements)

References 75 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Although the exact nature of the active species involved in the reaction is still unknown, a series of clues collected in previous investigations 2 prompted us to hypothesize a mechanism in which, after an initial outer-sphere oxidation of Fe II to Fe III , the temporary detachment of one of the pyridine arms would unmask the iron centre, which could be available to take part to the oxidation process, generating an initial Fe III –OOH based species (Fig. S23 † ).…”

Section: Resultsmentioning

confidence: 99%

“… 6 However, whichever the active species is, many pieces of evidence have been collected pointing to a controlled oxidation mechanism where free radical oxidations do not play any role. 2 …”

Section: Resultsmentioning

confidence: 99%

“…Was prepared according to the literature procedure 2 and spectral data were in accordance with those reported.…”

Section: Methodsmentioning

confidence: 99%

“…The chance of a direct installation of a heteroatom on non-activated positions has opened new synthetic routes and methodologies. 1 In particular, our attention was ultimately oriented to the sustainable oxygenation of aliphatic and aromatic C–H bonds carried out with green terminal oxidants such as hydrogen peroxide (H 2 O 2 ) in the presence of non-heme iron complexes 2 based on the imine function. 3,4 The choice of this kind of catalyst was guided by a series of needs: (i) use of an abundant and environmentally friendly metal, (ii) easy and (iii) cheap preparation of the catalyst.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Was prepared according to the literature procedure 2 and spectral data were in accordance with those reported.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…However, for more activated polycyclic substrates with lower BDEs of the benzylic C-H bond, the chemoselectivity decreased. 218 A mechanism for H 2 O 2 activation and substrate oxidation by complex 22 has been proposed…”

Section: Iron-catalyzed Arene Oxidationmentioning

confidence: 99%

Manganese and Nickel Complexes as Catalysts for Aromatic Oxidation

Rius¹

View full text Add to dashboard Cite

The development of selective aromatic oxidation catalysts based on non-noble metals has emerged over the last decades, mainly due to the importance of phenol products as intermediates for the generation of pharmaceuticals or functional polymers. In nature, metalloenzymes can perform a wide variety of oxidative processes using molecular oxygen, including arene oxidations, however, the implementation of such enzymes in the chemical industry remains challenging. In this context, chemists have tried to mimic nature and design synthetic non-noble metal catalysts inspired by these enzymes. This introduction chapter aims at providing a general overview on aromatic oxidation reactions catalyzed by metalloenzymes as well as synthetic first-row transition-metal complexes as homogeneous catalysts. The enzymes and complexes discussed in this chapter have been classified on the basis of the transition-metal ion present in their active site, i.e., iron, copper, nickel, and manganese. The main points of discussion focus on enzyme structure and function, catalyst design, mechanism of operation in terms of oxidant activation and substrate oxidation, and substrate scope. At the end of the chapter, the aim and scope of this thesis is outlined.

show abstract

Transition Metal Catalysts Bearing Multidentate Ligands for Efficient and Environmental Benign Oxidations by H₂O₂

et al. 2023

Self Cite

View full text Add to dashboard Cite

In this perspective, two different classes of multidentate ligands (aminotriphenolate and dipyridinimine) and the corresponding metal (Ti, V, Mo, W, Fe) complexes are described. These catalysts can activate efficiently the environmental benign H 2 O 2 oxidant, promoting a wide variety of oxidative processes (sulfoxidations, N-oxidations, epoxidations, haloperoxidation, alcohol oxidation, hydroxylation).

show abstract

Insight into the chemoselective aromaticvs.side-chain hydroxylation of alkylaromatics with H₂O₂catalyzed by a non-heme imine-based iron complex

Abstract: The oxidation of a series of alkylaromatic compounds with H2O2 catalyzed by an imine non-heme-iron complex prepared in situ by reaction of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 in a 2:2:1 ratio...

Cited by 7 publications

References 75 publications

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

Manganese and Nickel Complexes as Catalysts for Aromatic Oxidation

Transition Metal Catalysts Bearing Multidentate Ligands for Efficient and Environmental Benign Oxidations by H₂O₂

Contact Info

Product

Resources

About

Insight into the chemoselective aromaticvs.side-chain hydroxylation of alkylaromatics with H2O2catalyzed by a non-heme imine-based iron complex

Abstract: The oxidation of a series of alkylaromatic compounds with H2O2 catalyzed by an imine non-heme-iron complex prepared in situ by reaction of 2-picolylaldehyde, 2-picolylamine, and Fe(OTf)2 in a 2:2:1 ratio...

Cited by 7 publications

References 75 publications

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

Increasing the steric hindrance around the catalytic core of a self-assembled imine-based non-heme iron catalyst for C–H oxidation

Manganese and Nickel Complexes as Catalysts for Aromatic Oxidation

Transition Metal Catalysts Bearing Multidentate Ligands for Efficient and Environmental Benign Oxidations by H2O2

Contact Info

Product

Resources

About

Insight into the chemoselective aromaticvs.side-chain hydroxylation of alkylaromatics with H₂O₂catalyzed by a non-heme imine-based iron complex

Transition Metal Catalysts Bearing Multidentate Ligands for Efficient and Environmental Benign Oxidations by H₂O₂