2-Pyridyl Sulfoxide Directed Pd(II)-Catalyzed C–H Olefination of Arenes with Molecular Oxygen as the Sole Oxidant

Synthesis ◽  
2021 ◽  
Author(s):  
M. Bhanuchandra ◽  
Mamta Yadav ◽  
Ram Singh Jat ◽  
Bibek Sarma
Keyword(s):  
Molecular Oxygen ◽  
Reaction Pathway ◽  
Environmentally Benign ◽  
Isotopic Studies ◽  
Directing Group ◽  
Activated Olefins

AbstractPd(II)-catalyzed C–H olefination of aryl 2-pyridyl sulfoxides with unactivated and activated olefins has been demonstrated. We employed environmentally benign and inexpensive molecular oxygen as the sole oxidant. The versatile nature of the 2-pyridyl sulfoxide directing group has been proven by its transformation to the sulfone functionality. Deuterium scrambling experiments and intramolecular kinetic isotopic studies were carried out to gain insights into the reaction pathway.

Biomimetic flavin-catalysed reactions for organic synthesis

2015 ◽  
Vol 13 (28) ◽  
pp. 7599-7613 ◽  
Author(s):  
H. Iida ◽  
Y. Imada ◽  
S.-I. Murahashi
Keyword(s):  
Hydrogen Peroxide ◽  
Catalytic Oxidation ◽  
Molecular Oxygen ◽  
Organic Synthesis ◽  
Environmentally Benign ◽  
Wide Scope ◽  
Biomimetic Catalysts ◽  
Mild Conditions ◽  
Related Compounds

Using simple riboflavin related compounds as biomimetic catalysts, catalytic oxidation of various substrates with hydrogen peroxide or molecular oxygen can be performed selectively under mild conditions. The principle of these reactions is fundamental and will provide a wide scope for environmentally benign future practical methods.

Photooxidation of Cyclohexane with Dioxygen in Acetonitrile in the Presence of Transition Metal Chlorides

1992 ◽  
Vol 57 (1) ◽  
pp. 107-112 ◽  
Author(s):  
Pavel Lederer ◽  
Galina V. Nizova ◽  
Marina M. Kats ◽  
Georgii B. Shuľpin
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Molecular Oxygen ◽  
Reaction Pathway ◽  
Oxidation States ◽  
Quantum Yields ◽  
Radiation Wavelength ◽  
Metal Chlorides ◽  
Active Complex ◽  
Oxo Complexes

Irradiation of cyclohexane solution in acetonitrile (λ = 300, 365, or 436 nm) in the presence of dioxygen and catalytic amounts of FeCl3, CuCl3, Na[AuCl4] or H2[PtCl]6 gives rise to cyclohexanol and cyclohexanone (after GLC). The quantum yields with respect to the products lie within the range of 0.01 to 0.05. The most efficient of the catalysts used is FeCl3, and the most efficient radiation wavelength is λ = 365 nm. A reaction pathway is suggested; it is assumed that the first step is photoexcitation of M-Cl followed by electron transfer from the ligand to the metal associated with the formation of the Cl. radical, which reacts (probably after solvation by the solvent) with RH giving R.. The Fe(II) species is oxidized by ROO., and the photocatalytically active complex is restored. Complexes with metals in low oxidation states (particularly in the case of Cu, Au and Pt), however, can react with molecular oxygen to give peroxo or oxo complexes, which can directly hydroxylate alkanes.

Atom-economical selenation of electron-rich arenes and phosphonates with molecular oxygen at room temperature

2018 ◽  
Vol 16 (47) ◽  
pp. 9243-9250 ◽  
Author(s):  
Samir Kumar Bhunia ◽  
Pritha Das ◽  
Ranjan Jana
Keyword(s):  
Molecular Oxygen ◽  
Room Temperature ◽  
Environmentally Benign

An environmentally benign selenation of electron-rich arenes and phosphonates is developed adopting a novel recycle–reuse–reduce strategy for selenol by oxygen.

scholarly journals Metal-free oxidative coupling of arylmethylamines with indoles: a simple, environmentally benign approach for the synthesis of 3,3′-bis(indolyl)methanes

RSC Advances ◽  
2020 ◽  
Vol 10 (39) ◽  
pp. 23254-23262
Author(s):  
Vikas D. Kadu ◽  
Sankala Naga Chandrudu ◽  
Mahesh G. Hublikar ◽  
Dattatraya G. Raut ◽  
Raghunath B. Bhosale
Keyword(s):  
Molecular Oxygen ◽  
Oxidative Coupling ◽  
Environmentally Benign ◽  
Metal Free

The efficient metal-free oxidative coupling of arylmethylamines with indoles has been developed using molecular oxygen as a green oxidant towards a novel rout of 3,3′-bis(indolyl)methanes (BIMs) synthesis.

Solvent effect on the reactivity of monosubstituted phenols towards singlet molecular oxygen (O2(1Δg)) in alkaline media

1993 ◽  
Vol 71 (8) ◽  
pp. 1247-1252 ◽  
Author(s):  
Marta Luiz ◽  
María I. Gutiérrez ◽  
Graciela Bocco ◽  
Norman A. García
Keyword(s):  
Molecular Oxygen ◽  
Rate Constant ◽  
Reaction Pathway ◽  
Aqueous Media ◽  
Solvent Polarity ◽  
Alkaline Media ◽  
Quantum Yields ◽  
Quenching Rate ◽  
Singlet Molecular Oxygen ◽  
Quenching Rate Constant

The influence of solvent polarity on the dye-sensitized photooxidation (singlet molecular oxygen (O2(1Δg)) mediated) of a series of para-substituted phenolates was studied. Kinetic evidence obtained shows that the overall and the pure chemical interactions, phenolate–O2(1Δg), depend on the solvent polarity in a different way. This is clearly reflected in the efficiency of O2(1Δg) photooxidation of the substrates: surprisingly, the photooxidation quantum yield increases as the overall quenching rate constant decreases. The substrate photooxidation quantum yields obtained ranged from 0.05 to 0.15, the upper limit corresponding to a moderately polar medium (a benzene–methanol mixture) and the lower to an aqueous medium. We conclude that a high solvent polarity favours only the obtainment of the encounter complex (O2(1Δg)–phenolate), whereas the reactive step is affected in much the same way as those processes where charges are neutralized along the reaction pathway. The results obtained are discussed in terms of a partly polar excited state complex between O2(1Δg) and the phenolates. The rate constant for the reactive pathway in both organic and aqueous media is correlated with the Hammet-type substituent constant R−.

Aerobic photooxidative synthesis of 2-aryl-4-quinazolinones from aromatic aldehydes and aminobenzamide using catalytic amounts of molecular iodine

RSC Advances ◽  
2015 ◽  
Vol 5 (78) ◽  
pp. 63952-63954 ◽  
Author(s):  
Y. Nagasawa ◽  
Y. Matsusaki ◽  
T. Nobuta ◽  
N. Tada ◽  
T. Miura ◽  
...  
Keyword(s):  
Visible Light ◽  
Molecular Oxygen ◽  
Visible Light Irradiation ◽  
Aromatic Aldehydes ◽  
Catalytic Amount ◽  
Molecular Iodine ◽  
Light Irradiation ◽  
Environmentally Benign ◽  
Synthetic Method

This study reports a safe, mild, and environmentally benign synthetic method toward 2-aryl-4-quinazolinones through a cyclization–oxidation sequence using a catalytic amount of iodine, harmless visible light irradiation, and molecular oxygen.

Ruthenium-Catalyzed Annulation of N-Cbz Hydrazones via C–H/N–N Bond Activation for the Rapid Synthesis of Isoquinolines

Synthesis ◽  
2019 ◽  
Vol 51 (12) ◽  
pp. 2506-2514 ◽  
Author(s):  
Dewal S. Deshmukh ◽  
Bhalchandra M. Bhanage
Keyword(s):  
Functional Group ◽  
Bond Activation ◽  
Strategy Use ◽  
Environmentally Benign ◽  
Catalyst Loading ◽  
Green Solvent ◽  
Rapid Synthesis ◽  
Ru Catalyst ◽  
Internal Alkynes ◽  
Directing Group

In this work, N-Cbz hydrazone has been employed as a rarely explored directing group for the synthesis of isoquinolines by annulation with internal alkynes via C–H/N–N activation using Ru catalyst. Additive as well as external oxidant-free rapid protocol has been established for the synthesis of isoquinolines using microwave strategy. Use of non-volatile and biodegradable PEG as a green solvent with lower catalyst loading makes the proposed protocol environmentally benign. Further, higher functional group tolerance and wide substrate scope has been observed under the stated methodology with higher yields.

Environmentally benign multiphase solid–liquid–gas catalysis

2020 ◽  
Vol 22 (3) ◽  
pp. 895-902
Author(s):  
Xueli Bai ◽  
Nianze Song ◽  
Liang Wen ◽  
Xin Huang ◽  
Jian Zhang ◽  
...  
Keyword(s):  
Heavy Metal ◽  
Molecular Oxygen ◽  
Environmentally Benign ◽  
Oxidation Reactions ◽  
Solid Liquid

It is significant for the environment that molecular oxygen replaces conventional heavy metal-containing or toxic oxidants to participate in oxidation reactions.

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