Fe(NO3)3·9H2O-catalyzed aerobic oxidative deoximation of ketoximes and aldoximes under mild conditions

2018 ◽  
Vol 96 (8) ◽  
pp. 810-814 ◽  
Author(s):  
Yongshu Li ◽  
Nizhou Xu ◽  
Guangyao Mei ◽  
Yun Zhao ◽  
Yiyong Zhao ◽  
...  
Keyword(s):  
Molecular Oxygen ◽  
Functional Groups ◽  
Environmentally Benign ◽  
Synthetic Method ◽  
Simple Process ◽  
Practical Applications ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Wide Range ◽  
Plausible Mechanism

A mild, simple process for the effective aerobic oxidative deoximation of a wide range of ketoximes and aldoximes has been developed that utilizes Fe(NO3)3·9H2O as the single catalyst and molecular oxygen as the green oxidant. The environmentally benign protocol provides moderate to excellent yield and broad functional groups tolerance and is a valuable synthetic method for practical applications. According the relevant verification experiment, a plausible mechanism has been proposed.

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

Synlett ◽  
2020 ◽  
Vol 31 (16) ◽  
pp. 1629-1633
Author(s):  
K. Sunil ◽  
Merla Arjuna Rajendra ◽  
Ayyiliath Meleveetil Sajith ◽  
Muthipeedika Nibin Joy ◽  
Vasiliy A. Bakulev ◽  
...  
Keyword(s):  
Environmentally Benign ◽  
Potassium Hexacyanoferrate ◽  
Mild Conditions ◽  
Suitable Substrate ◽  
Wide Range ◽  
Palladium Catalyzed

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

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.

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.

Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides

Synlett ◽  
2020 ◽  
Vol 31 (11) ◽  
pp. 1087-1093 ◽  
Author(s):  
Jianbo Zhang ◽  
Youxian Dong ◽  
Madina Yuma ◽  
Yuling Mei ◽  
Nan Jiang ◽  
...  
Keyword(s):  
Amino Acids ◽  
Stereoselective Synthesis ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Additional Ligand

An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without additional ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcohols, amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

Original disymmetric bolaforms bearing at least one sulfobetaine head; synthesis and surface properties

2001 ◽  
Vol 79 (7) ◽  
pp. 1153-1158 ◽  
Author(s):  
Souad Souirti ◽  
Michel Baboulène
Keyword(s):  
Surface Properties ◽  
Functional Groups ◽  
Efficient Method ◽  
Aqueous Media ◽  
Critical Micellar Concentration ◽  
Excellent Yield ◽  
Wide Range ◽  
Self Aggregation ◽  
Cationic Amphiphile

We describe a simple and efficient method for the synthesis of disymmetric bolaforms bearing at least one sulfobetaine head. In this process, we could introduce successively on α, ω-bis(dialkylamino) alkane a sulfobetaine head and a cationic, a sulfobetaine, or a carboxybetaine head, in excellent yield. This is the first synthesis of disymmetric sulfobetaine bolaforms. The method is easily generalized to various types of head functional groups. The wide range of bolaforms produced by this method has been exploited to study their surface properties and to determine the respective roles of the polar heads and the lengths of the spacers (n) on self-aggregation in aqueous media. A critical micellar concentration (cmc) was observed with the compounds with a spacer of 12 carbon atoms (n = 12). Micellization appeared to be consistent with a "wicket-like" conformation, which did not appear to form with the n = 8 compounds.Key words: disymmetric bolaform, sulfobetaine, carboxybetaine, cationic amphiphile, synthesis, surface properties.

A Selective and Versatile Synthesis of Substituted Chromones via Addition of Phenols to Dimethyl Acetylenedicarboxylate

1995 ◽  
Vol 48 (3) ◽  
pp. 677 ◽  
Author(s):  
MJ Stoermer ◽  
DP Fairlie
Keyword(s):  
Functional Groups ◽  
Addition Reaction ◽  
Initial Step ◽  
High Yield ◽  
Selective Synthesis ◽  
Dimethyl Acetylenedicarboxylate ◽  
Substituted Phenols ◽  
Valuable Component ◽  
Mild Conditions ◽  
Wide Range

Despite many published syntheses of chromones, none has been reported to be both selective for chromones and tolerant of ring substitution. The addition of substituted phenols to dimethyl acetylenedicarboxylate is now reported as a versatile high yield initial step in a simple three-step synthesis of chromone 2-carboxylic acids. Triethylamine being used to deprotonate the substituted phenol, the addition to dimethyl acetylenedicarboxylate proceeds under mild conditions and tolerates a wide range of functional groups on the phenol. Although not stereoselective, both fumarate and maleate aryloxy products of this addition can then be cyclized, according to a known method, to chromones without contamination by isomeric coumarins. Thus the addition reaction is a valuable component of a versatile and selective synthesis of substituted chromones.

A Practical Access to Functionalized Alkyl Sulfinates

Synlett ◽  
2018 ◽  
Vol 29 (12) ◽  
pp. 1622-1626
Author(s):  
M. Haddad ◽  
P. Phansavath ◽  
V. Ratovelomanana-Vidal ◽  
C. Tran ◽  
B. Flamme ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cost Effective ◽  
Good Tolerance ◽  
Mild Conditions ◽  
Cost Effective Method ◽  
Wide Range

We describe herein a three-step synthesis of aliphatic sulfinates. This cost-effective method involves the use of 2-mercaptobenzothiazole under mild conditions and exhibits good yields (up to 78% over three steps). This approach provides an access to a wide range of functionalized sulfinates. A good tolerance with respect to diverse functional groups (alkene, alkyne, ether, acetal) was also noted.

Kinetics and mechanism of the oxidation of tris(4,7-dihydroxy-1,10-phenanthroline)-iron(II) by molecular oxygen

1980 ◽  
Vol 58 (17) ◽  
pp. 1773-1779 ◽  
Author(s):  
Flora T. T. Ng ◽  
Patrick M. Henry
Keyword(s):  
Electron Transfer ◽  
Molecular Oxygen ◽  
Reactive Species ◽  
Kinetics And Mechanism ◽  
Ph Profile ◽  
Rate Law ◽  
Notable Feature ◽  
Wide Range ◽  
Naoh Solution ◽  
Plausible Mechanism

The reaction of (OHP)3Fe(II) (OHP = 4,7-dihydroxy-1,10-phenanthroline) with oxygen in aqueous 0.1 N NaOH solution takes place according to the stoichiometry:[Formula: see text]This stoichiometry holds whether (OHP)3Fe(II) or O2 is in excess. The rate law over a wide range of (OHP)3Fe(II) and O2 concentrations at 0.1 N NaOH has the form:[Formula: see text]A notable feature of this oxidation is that free HO2− is not produced as an intermediate. A plausible mechanism involving bound superoxide or peroxide as intermediates is proposed. Due to the redox nature of the OHP ligand and the low potenial of the (OHP)3Fe(II) complex, a 4 electron transfer from one (OHP)3Fe(II) to one O2 to give a Fe(IV) species with an oxidized ligand is a distinct possibility. The rate–pH profile is consistent with the protonation of (OHP)3Fe(II) (pKa ≈ 9.4) to give a more reactive species.

scholarly journals Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2969
Author(s):  
Guipeng Feng ◽  
Guoyang Ma ◽  
Wenyan Chen ◽  
Shaohong Xu ◽  
Kaikai Wang ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Functional Groups ◽  
Absolute Configuration ◽  
Dipolar Cycloaddition ◽  
Quantum Electronic ◽  
Mild Conditions ◽  
Spectrum Method ◽  
Wide Range ◽  
Reaction Proceeds ◽  
Azomethine Imines

[3 + 2] A 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.

A clean and simple method for deprotection of phosphines from borane complexes

2018 ◽  
Vol 90 (1) ◽  
pp. 49-62 ◽  
Author(s):  
Oleg M. Demchuk ◽  
Radomir Jasinski ◽  
Dorota Strzelecka ◽  
Kamil Dziuba ◽  
Karolina Kula ◽  
...  
Keyword(s):  
Functional Groups ◽  
Phosphorus Atom ◽  
Kinetic Data ◽  
Reaction Conditions ◽  
Simple Method ◽  
Mild Conditions ◽  
Excellent Yield ◽  
Tertiary Phosphines ◽  
Quantumchemical Calculations ◽  
First Time

AbstractSimple, efficient, clean, and stereospecific protocols of protection of phosphorus atom with borane and deprotection from the borane complexes of the tertiary phosphines in mild conditions are reported. The proposed protection/deprotection reactions tolerate a range of functional groups and lead to pure products with excellent yield with no need for application of chromatographic or crystallisation purification procedures. For the first time mechanisms of the reactions of phosphine protection and deprotection have been studied based on experimental kinetic data as well as quantumchemical calculations, which allows designing reaction conditions suitable for a given substrate.

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