Understanding the reaction mechanisms of Pd-catalysed oxidation of alcohols and domino oxidation–arylation reactions using phenyl chloride as an oxidant

2014 ◽  
Vol 1 (10) ◽  
pp. 1188-1196 ◽  
Author(s):  
Yang Li ◽  
Zhenyang Lin
Keyword(s):  
Reaction Mechanisms ◽  
Oxidation Reactions ◽  
Catalysed Oxidation ◽  
Oxidation Of Alcohols

The Pd-catalysed oxidation reactions of alcohols and their domino oxidation–arylation reactions using phenyl chloride as an oxidant have been computationally investigated.

scholarly journals β-Ketophosphonates with Pentalenofuran Scaffolds Linked to the Ketone Group for the Synthesis of Prostaglandin Analogs

2021 ◽  
Vol 22 (13) ◽  
pp. 6787
Author(s):  
Constantin I. Tănase ◽  
Constantin Drăghici ◽  
Miron Teodor Căproiu ◽  
Anamaria Hanganu ◽  
Gheorghe Borodi ◽  
...  
Keyword(s):  
Lithium Salt ◽  
Methyl Esters ◽  
Secondary Compounds ◽  
Molecular Structures ◽  
Keto Group ◽  
High Yield ◽  
Oxidation Reactions ◽  
Prostaglandin Analogues ◽  
X Ray ◽  
Oxidation Of Alcohols

β-Ketophosphonates with pentalenofurane fragments linked to the keto group were synthesized. The bulky pentalenofurane skeleton is expected to introduce more hindrance in the prostaglandin analogues of type III, greater than that obtained with the bicyclo[3.3.0]oct(a)ene fragments of prostaglandin analogues I and II, to slow down (retard) the inactivation of the prostaglandin analogues by oxidation of 15α-OH to the 15-keto group via the 15-PGDH pathway. Their synthesis was performed by a sequence of three high yield reactions, starting from the pentalenofurane alcohols 2, oxidation of alcohols to acids 3, esterification of acids 3 to methyl esters 4 and reaction of the esters 4 with lithium salt of dimethyl methanephosphonate at low temperature. The secondary compounds 6b and 6c were formed in small amounts in the oxidation reactions of 2b and 2c, and the NMR spectroscopy showed that their structure is that of an ester of the acid with the starting alcohol. Their molecular structures were confirmed by single crystal X-ray determination method for 6c and XRPD powder method for 6b.

Oscillatory phenomena in heterogeneous catalysed oxidation reactions

Catalysis ◽  
2007 ◽  
pp. 1-26 ◽  
Author(s):  
D. Mukesh ◽  
M. Goodman ◽  
C. M. Kenney ◽  
W. Morton
Keyword(s):  
Oxidation Reactions ◽  
Catalysed Oxidation

Table salt as a catalyst for the oxidation of aromatic alcohols and amines to acids and imines in aqueous medium: effectively carrying out oxidation reactions in sea water

2019 ◽  
Vol 21 (8) ◽  
pp. 1929-1934 ◽  
Author(s):  
Susanta Hazra ◽  
Ajay Kishor Kushawaha ◽  
Deepak Yadav ◽  
Pritam Dolui ◽  
Mayukh Deb ◽  
...  
Keyword(s):  
Aqueous Medium ◽  
Carboxylic Acids ◽  
Sea Water ◽  
Oxidation Reactions ◽  
Table Salt ◽  
Economical Method ◽  
Oxidation Of Alcohols ◽  
Aromatic Alcohols

A simple, efficient, sustainable and economical method for the oxidation of alcohols and amines has been developed using chloride, a sea abundant anionic catalyst for the synthesis of a range of carboxylic acids, ketones and imines.

Ruthenium-catalysed oxidation of alcohols to amides using a hydrogen acceptor

Tetrahedron ◽  
2014 ◽  
Vol 70 (23) ◽  
pp. 3683-3690 ◽  
Author(s):  
Andrew J.A. Watson ◽  
Russell J. Wakeham ◽  
Aoife C. Maxwell ◽  
Jonathan M.J. Williams
Keyword(s):  
Hydrogen Acceptor ◽  
Catalysed Oxidation ◽  
Oxidation Of Alcohols

Cytochrome P-450 model reaction: effects of substitution on the rate of aromatic hydroxylation

2000 ◽  
Vol 04 (03) ◽  
pp. 285-291 ◽  
Author(s):  
NASSER SAFARI ◽  
FARZAD BAHADORAN ◽  
MOHAMMAD REZA HOSEINZADEH ◽  
REZA GHIASI
Keyword(s):  
Relative Rate ◽  
Kinetic Method ◽  
Oxidation Reactions ◽  
Aromatic Rings ◽  
Aromatic Hydroxylation ◽  
Catalysed Oxidation ◽  
Epoxidation Of Alkenes ◽  
Cytochrome P 450 ◽  
Related Compounds ◽  
Electron Withdrawing Substituents

The study of haemin-catalysed oxidation reactions was extended to substituted aromatic rings. Both electron-donating and electron-withdrawing substituents on aromatic rings act as para- and meta-directing agents in the presence of tetrakis(2,6-dichlorophenyl)porphyrin iron(III) chloride as catalyst and m-chloroperbenzoic acid as oxidant. A new kinetic method for measuring relative rates of epoxidation of alkenes and related compounds has been developed; while steric hindrance results in decreasing the rate of hydroxylation, electron-rich and electron-withdrawing substituents were found to increase the rate of hydroxylation. A linear relationship between the logarithm of the relative rate of hydroxylation and σ Hammet is obtained, although electron-donating and electron-withdrawing substituents fit separate lines. Addition of pyridine to haemin was shown to increase the yield of epoxidation but decrease the yield of aromatic hydroxylation.

scholarly journals A Bio-Inspired Lanthanum-Ortho Quinone Catalyst for Aerobic Oxidation of Alcohol

2020 ◽  
Author(s):  
Ruipu Zhang ◽  
Long Zhang ◽  
Ming-Tian Zhang ◽  
Sanzhong Luo
Keyword(s):  
Aerobic Oxidation ◽  
Earth Metal ◽  
Open Shell ◽  
Oxidation Catalysis ◽  
Oxidation Catalyst ◽  
Oxidation Reactions ◽  
Reductive Activation ◽  
Ambient Conditions ◽  
Semiquinone Radicals ◽  
Oxidation Of Alcohols

<p>Oxidation reactions are fundamental transformations in organic synthesis and chemical industry. With oxygen or air as terminal oxidant, aerobic oxidation catalysis provides the most sustainable and economic oxidation processes. Most aerobic oxidation catalysis employs redox metal as its active center. While nature provides non-redox metal strategy as in pyrroloquinoline quinone (PQQ)-dependent methanol dehydrogenases (MDH), such an effective chemical version is unknown. Inspired by the recently discovered rare earth metal-dependent enzyme Ln-MDH, here we show that an open-shell semi-quinone anionic radical species in complexing with lanthanum could serve as a very efficient aerobic oxidation catalyst under ambient conditions. In this catalyst, the lanthanum metal serves only as a Lewis acid promoter and the redox process occurs exclusively on the semiquinone ligand. The catalysis is initiated by 1e<sup>-</sup>-reduction of lanthanum-activated <i>ortho</i>-quinone to a semiquinone-lanthanum complex La(<b>SQ<sup>-.</sup></b>)<sub>2</sub>, which undergoes a coupled O-H/C-H dehydrogenation for aerobic oxidation of alcohols with up to 330 h<sup>-1</sup> TOF. This study suggests a possible functional mode of semiquinone radicals, widely observed with quinoproteins in Nature. Moreover, this unique reductive activation strategy as well as the resulted radical anion as redox ligand creates a new turning point in the development of efficient aerobic oxidation catalysis.</p>

scholarly journals Fe(II)-phthalocyanine supported on chitosan aerogel as a catalyst for oxidation of alcohols and alkyl arenes

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Fatemeh Azimi ◽  
Ahmad Poursattar Marjani ◽  
Sajjad Keshipour
Keyword(s):  
Aspect Ratio ◽  
Heterogeneous Catalyst ◽  
High Aspect Ratio ◽  
Room Temperature ◽  
Oxidation Reactions ◽  
Mild Conditions ◽  
Oxidation Of Alcohols ◽  
Aromatic Alcohols ◽  
Aldehydes And Ketones ◽  
Low Toxicity

AbstractManipulation of materials is considered as one of the eminent strategies to create desirable catalysts. In this regard, increasing surface area and decreasing dimensions of catalysts have been widely employed on account of effectiveness of these methods. Herein, aerogel form of chitosan as a sustainable, and high aspect ratio compound is employed as a green support for the catalytic purposes. Chitosan aerogel was modified with Fe(II)-phthalocyanine to produce a heterogeneous catalyst for oxidation reactions. The synthesized catalyst promoted the oxidation reactions of alcohols and alkyl arenes to the corresponding aldehydes and ketones using H2O2 as an oxidant in 24 h. The reactions for aliphatic and aromatic alcohols gave turnover numbers of 106–109 at 80 °C and 106–117 at room temperature, respectively. The oxidations of alkyl arenes were carried out with turnover numbers laying in the range of 106–117 at 100 °C. The low toxicity, inexpensive nature, and recycling possibility of the catalyst accompanied by the reaction mild conditions, clean oxidant, and excellent yields offer chitosan aerogel modified with Fe(II)-phthalocyanine as a promising catalyst for oxidation reactions.

Visible-light-driven photocatalytic selective organic oxidation reactions

2020 ◽  
Vol 8 (40) ◽  
pp. 20897-20924 ◽  
Author(s):  
Xue Yang ◽  
Suyuan Zhang ◽  
Peixian Li ◽  
Shuiying Gao ◽  
Rong Cao
Keyword(s):  
Visible Light ◽  
Future Development ◽  
Reaction Mechanisms ◽  
Oxidation Reactions ◽  
Development Trends ◽  
Recent Advances ◽  
The Future ◽  
Visible Light Driven ◽  
Organic Oxidation ◽  
Made In

In this review, we focus on the most recent advances made in visible-light-driven selective organic oxidation transformations and highlighted their reaction mechanisms. Moreover, we discuss the future development trends, challenges, and prospective outlook in detail.

scholarly journals Differentiation between Enamines and Tautomerizable Imines Oxidation Reaction Mechanism using Electron-Vibration-Vibration Two Dimensional Infrared Spectroscopy

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 869 ◽  
Author(s):  
Fengqin Long ◽  
Zheng Chen ◽  
Keli Han ◽  
Lu Zhang ◽  
Wei Zhuang
Keyword(s):  
Reaction Mechanism ◽  
Reaction Mechanisms ◽  
Theoretical Calculations ◽  
Two Dimensional ◽  
Oxidation Reactions ◽  
Spectral Signatures ◽  
Potential Strength ◽  
Chemical Reaction Mechanisms ◽  
2Dir Spectroscopy ◽  
Two Dimensional Infrared Spectroscopy

Intermediates lie at the center of chemical reaction mechanisms. However, detecting intermediates in an organic reaction and understanding its role in reaction mechanisms remains a big challenge. In this paper, we used the theoretical calculations to explore the potential of the electron-vibration-vibration two-dimensional infrared (EVV-2DIR) spectroscopy in detecting the intermediates in the oxidation reactions of enamines and tautomerizable imines with 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO). We show that while it is difficult to identify the intermediates from their infrared and Raman signals, the simulated EVV-2DIR spectra of these intermediates have well resolved spectral features, which are absent in the signals of reactants and products. These characteristic spectral signatures can, therefore, be used to reveal the reaction mechanism as well as monitor the reaction progress. Our work suggests the potential strength of EVV-2DIR technique in studying the molecular mechanism of organic reactions in general.

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