Vanadium(V) complexes with chiral tridentate Schiff base ligands derived from 1S,2R(+)-2-amino-1,2-diphenylethanol and with acetohydroxamate co-ligand: Synthesis, characterization and catalytic activity in the oxidation of prochiral sulfides and olefins

Romanowski, Grzegorz; Kira, Jaromir; Wera, Michał

doi:10.1016/j.molcata.2013.10.011

Cited by 30 publications

(12 citation statements)

References 57 publications

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“…In a series of publications, Romanowski and co-workers prepared and X-ray characterized a series of dimeric oxovanadium(V) complexes of the general formula [L*(O)V–O–V(O)L*] (where L* is a chiral Schiff base of the type 115 ), − which exhibited generally moderate enantioselectivities in the oxidation of methyl phenyl sulfide and benzyl phenyl sulfide at room temperature; at −20 °C, the former could be oxidized with up to 90% yield and 94% ee …”

Section: Asymmetric Sulfoxidation Reactionsmentioning

confidence: 99%

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂

2017

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The discovery of simple and efficient catalyst systems for the asymmetric oxofunctionalization of hydrocarbons is a challenging task of catalytic chemistry. In this paper, we give an overview of catalyst systems capable of conducting asymmetric oxygenative transformations of organic molecules and, in line with the major trend to sustainability, relying on green oxidants HO and O as the ultimate oxygen source. The full historical period of asymmetric oxidation catalysis (1970 to the present day) is covered; both transition-metal-based and organocatalytic systems are considered. The focus of this review is the catalytic properties of the existing catalyst systems, in particular stereoselectivity, activity, efficiency, and synthetic outlook. At the same time, mechanistic peculiarities of stereoselective oxygen transfer are given attention.

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Section: Asymmetric Sulfoxidation Reactionsmentioning

confidence: 99%

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂

2017

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“…Moreover, oxidative cleavages can be also found at advanced stages of routes toward products of interest (Grandilodine C alkaloid, Penifulvin B and C sesquiterpenoids, and neuroactive benz[ e ]indenes, inter alia) . The toxicity and potential risk of ozone and other oxidants and the stoichiometric amounts of waste generated from the use of other oxidizing agents (KMnO 4 , NaIO 4 , TBHP, OsO 4 , oxone, I(III) reagents) , have encouraged the search for more sustainable reagents.…”

Section: Introductionmentioning

confidence: 99%

Aerobic Cleavage of Alkenes and Alkynes into Carbonyl and Carboxyl Compounds

et al. 2017

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This review provides an overview of the recent developments on the oxygen-mediated cleavage of olefins and acetylene derivatives to provide carbonyl and carboxylic compounds. A number of photo, organo, and metal catalysts have been reviewed with an emphasis on those exhibiting superior performance. For this purpose, crucial aspects such as pressure, substrate scope, product selectivity for the target aldehydes, ketones, or carboxylic acids, catalyst amount, and recyclability are discussed. Although many improvements are required to match the results provided by conventional oxidants, aerobic cleavage of such unsaturated hydrocarbons is a very promising field in progress on account of the significant achievements extracted from the recent literature. Several postulated mechanisms are also provided to gain insight into the role of the catalysts and the incorporation of oxygen atoms into the products.

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“…Romanowski and co-workers have provided several reports utilizing vanadium(V) complexes with tridentate Schiff base ligands (similar to those employed earlier by Junnosuke and co-workers) for sulfide oxidation. − For these systems, they propose a mechanism similar to that in Scheme but which also includes initial coordination of sulfur to the vanadium center, demonstrating the stark effects of oxidant and substrate choice. However, the formation of a biradical intermediate was not discussed in the original manuscript.…”

Section: Catalytic Applications Of Homogeneous Vanadium Systemsmentioning

confidence: 79%

Catalytic Applications of Vanadium: A Mechanistic Perspective

et al. 2018

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The chemistry of vanadium has seen remarkable activity in the past 50 years. In the present review, reactions catalyzed by homogeneous and supported vanadium complexes from 2008 to 2018 are summarized and discussed. Particular attention is given to mechanistic and kinetics studies of vanadium-catalyzed reactions including oxidations of alkanes, alkenes, arenes, alcohols, aldehydes, ketones, and sulfur species, as well as oxidative C–C and C–O bond cleavage, carbon–carbon bond formation, deoxydehydration, haloperoxidase, cyanation, hydrogenation, dehydrogenation, ring-opening metathesis polymerization, and oxo/imido heterometathesis. Additionally, insights into heterogeneous vanadium catalysis are provided when parallels can be drawn from the homogeneous literature.

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Vanadium(V) complexes with chiral tridentate Schiff base ligands derived from 1S,2R(+)-2-amino-1,2-diphenylethanol and with acetohydroxamate co-ligand: Synthesis, characterization and catalytic activity in the oxidation of prochiral sulfides and olefins

Cited by 30 publications

References 57 publications

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂

Aerobic Cleavage of Alkenes and Alkynes into Carbonyl and Carboxyl Compounds

Catalytic Applications of Vanadium: A Mechanistic Perspective

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Vanadium(V) complexes with chiral tridentate Schiff base ligands derived from 1S,2R(+)-2-amino-1,2-diphenylethanol and with acetohydroxamate co-ligand: Synthesis, characterization and catalytic activity in the oxidation of prochiral sulfides and olefins

Cited by 30 publications

References 57 publications

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2and O2

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2and O2

Aerobic Cleavage of Alkenes and Alkynes into Carbonyl and Carboxyl Compounds

Catalytic Applications of Vanadium: A Mechanistic Perspective

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Product

Resources

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Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂

Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H₂O₂and O₂