Vanadium catalyzed aerobic carbon–carbon cleavage

Amadio, Emanuele; Lorenzo, Rosalia Di; Zonta, Cristiano; Licini, Giulia

doi:10.1016/j.ccr.2015.06.004

Cited by 66 publications

(40 citation statements)

References 83 publications

(110 reference statements)

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“…For instance, vanadate and vanadyl derivatives possess significant importance as biologically active species, [1,2] have been shown to possessi nsulin-mimetic properties [3][4][5][6] and are important catalytic species in variouso xidation reactions. [7][8][9] In contrast, non-oxido vanadium(IV) compounds are less frequently reported in the literature. Sproules, Wieghardt and co-workersd escribed V IV complexesw ith non-innocent ligand-sets.…”

Section: Introductionmentioning

confidence: 99%

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Schlüter

Kleemiss

Fugel

et al. 2020

Chemistry A European J

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Derivatives of 1,2-dithienylethene (DTE)h ave superb photochromic properties due to an efficient reversible photocyclization reaction of their hexatriene structure and, thus, have application potential in materials for optoelectronics and (multi-responsive) molecular switches. Transition-metal complexes bearing switchable DTE motifsc ommonly incorporate their coordination site ratherd istantf rom the hexatriene system.I nt his work the redoxa ctive ligand 1,2-bis(2,5-dimethylthiophen-3-yl)ethane-1,2-dione is described,w hich reacts with [V(TMEDA) 2 Cl 2 ]t og ive ar are nonoxido vanadium(IV) species 3(M,M/P,P).T his blue complex has two bidentate en-diolato ligandsw hich chelate the V IV center and give rise to two five-membered metallacycles with the adjacent hexatriene DTE backboneb earing axial chirality.U pon irradiation with UVAl ight or prolonged heating in solution, the blue compound 3(M,M/P,P) converts into the purple atropisomer 4(para,M/para,P).B othc omplexes were isolated and structurally characterized by single-crystal X-ray diffraction analysis (using lab source and synchrotron radiation). The antiparallel configuration( M or P helicity) present in both 3(M,M/P,P) and 4(para,M/para,P) is aprerequisite for (reversible)6 p cyclization reactions. AC WE PR spectroscopic study reveals the metalloradical character for 3(M,M/P,P) and 4(para,M/para,P) and indicatesd ynamic reversible cyclization of the DTE backbonei nc omplex 3(M,M/ P, P ) at ambient temperature in solution.

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Section: Introductionmentioning

confidence: 99%

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Schlüter

Kleemiss

Fugel

et al. 2020

Chemistry A European J

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“…Several metal-containing catalysts were assessed for the aerobic oxidative cleavage of lignin [3,4]. One of the most used metals is vanadium [5][6][7]. Keggin-type phosphovanadomolybdic acids (H 3+x PMo 12−x V x O 40 , nH 2 O) noted H 3+x PV x [8][9][10] are among the vanadium-based catalysts reported.…”

Section: Introductionmentioning

confidence: 99%

Vanadium-Substituted Phosphomolybdic Acids for the Aerobic Cleavage of Lignin Models—Mechanistic Aspect and Extension to Lignin

2020

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This work deals with the aerobic oxidative cleavage of C-C and C-O bonds catalyzed by the Keggin-type phosphovanadomolybdic acid (H 6 [PMo 9 V 3 O 40 ], noted H 6 PV 3 ). The latter was synthesized by an adapted hydrothermal procedure classically used for lower vanadium content and was tested as a catalyst for the aerobic cleavage of 2-phenoxyacetophenone (noted K1 HH ) and 1-phenyl-2-phenoxyethanol (A1 HH ) used as two lignin models. The operative conditions (solvent, catalytic loading, etc.) were adjusted on K1 HH and extrapolated to A1 HH . The cleavage of the alcohol model required more drastic conditions and therefore further optimization. Preliminary attempts on an Organosolv wheat straw lignin were performed too. From the kinetic study, high performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS) data, a mechanism of the cleavage of both models was proposed.

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“…Catalytic oxidation by metal complexes is one of the most widely studied reactions in organic chemistry since epoxides are important synthetic intermediates for a wide variety of products . Oxovanadium complexes have been widely used as homogeneous and heterogeneous catalysts for reactions such as alkene epoxidations, sulfoxidation, alcohol oxidations, oxidative couplings, oxidative brominations, oxidative Strecker reactions, olefin polymerization and carbon–carbon cleavages …”

Section: Introductionmentioning

confidence: 99%

Synthesis of a new schiff base oxovanadium complex with melamine and 2‐hydroxynaphtaldehyde on modified magnetic nanoparticles as catalyst for allyl alcohols and olefins epoxidation

Farzaneh

Asgharpour

2019

Applied Organom Chemis

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A new magnetically recoverable nanocatalyst designated as Fe3O4@SiO2@PTMS@Mel‐Naph‐VOcomplex was synthesize by covalent binding of a Schiff base ligand derived from melamine and 2‐hydroxy1naphtaldehyde on the surface of silica coated iron oxide magnetic nanoparticles followed by complexation with VO (acac)2. Characterization of the prepared nanocatalyst was accomplished with FT‐IR, XRD, SEM, HRTEM, VSM and atomic absorption techniques. It was found that the epoxidation of geraniol, trans‐2‐hexen‐1‐ol, 1‐octen‐3‐ol, norbornene, and cyclooctene is highly selective, affording quantitative yields of the corresponding epoxides with tert‐butyl hydroperoxide (TBHP) using Fe3O4@SiO2@Mel‐Naph‐VOcomplex as catalyst. High reaction yields, short reaction times, simple experimental and work up procedure, catalyst stability and excellent reusability even after five‐cycles of usage in the case of geraniol are some advantages of this research.

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Vanadium catalyzed aerobic carbon–carbon cleavage

Cited by 66 publications

References 83 publications

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Non‐Oxido‐Vanadium(IV) Metalloradical Complexes with Bidentate 1,2‐Dithienylethene Ligands: Observation of Reversible Cyclization of the Ligand Scaffold in Solution

Vanadium-Substituted Phosphomolybdic Acids for the Aerobic Cleavage of Lignin Models—Mechanistic Aspect and Extension to Lignin

Synthesis of a new schiff base oxovanadium complex with melamine and 2‐hydroxynaphtaldehyde on modified magnetic nanoparticles as catalyst for allyl alcohols and olefins epoxidation

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