Nitration of N -acetyl anilides using silver(I) nitrate/persulfate combination DOI

Hathaichanok Sanjeam,

Chutima Kuhakarn,

Pawaret Leowanawat

et al.

Synthetic Communications, Journal Year: 2022, Volume and Issue: 52(9-10), P. 1279 - 1289

Published: May 19, 2022

Nitration of N-acetyl anilides using a simple combination AgNO3 and K2S2O8 as stable nitro source an oxidant, respectively, was explored. The reaction practical to operate proceeded under considerably mild conditions (reflux in acetonitrile) within acceptable time (6 h). para-substituted gave only ortho-nitrated products moderate good yields (30–63% yields). ortho-, meta-, or non-substituted mixture nitrated (30–72% combined yields) with preferentially at the para- over ortho-position (ortho:para; 1.0:1.1–1.0:2.8).

Language: Английский

Organic Nitrating Reagents DOI
Subrata Patra, Ivan Mosiagin, Dmitry Katayev

et al.

Synthesis, Journal Year: 2022, Volume and Issue: 54(15), P. 3432 - 3472

Published: April 13, 2022

Abstract Nitro compounds are vital raw chemicals that widely used in academic laboratories and industries for the preparation of various drugs, agrochemicals, materials. Thus, nitrating reactions great importance chemists even taught schools as one fundamental transformations organic synthesis. Since discovery first 19th century, progress this field has been constant. Yet, many years classical electrophilic nitration approach using a mixture strong mineral acids dominated field. However, recent decades, attention researchers focused on new reactivity reagents can provide access to nitro practical straightforward way under mild reaction conditions. Organic have played special role since they enhanced reactivity. They also allow be carried out an ecofriendly sustainable manner. This review examines development application reagents. 1 Introduction 2 Nitrating Reagents 2.1 Alkyl Nitrites 2.2 Nitroalkanes 2.3 Nitrates 2.4 N-Nitroamides 2.5 N-Nitropyrazole 2.6 N-Nitropyridinium Salts 3 Generated In Situ 3.1 Acyl 3.2 Trimethylsilyl Nitrate 3.3 Onium 4 Nitronium 5 5.1 Ammonium 5.2 Heteroarylium 5.3 Other 5.4 6 Conclusion Outlook

Language: Английский

Citations

42
Visible-Light-Initiated Difunctionalization of Quinoxalin-2(1H)-ones with Acyloxy Nitroso Compounds DOI

Runye Gao,

Fang Wang, Xiao Geng

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(39), P. 7118 - 7122

Published: Sept. 25, 2022

Herein, a photoinitiated radical relay reaction of quinoxalin-2(1H)-ones, with acyloxy nitroso compounds as source radicals, is described. Although the C-H functionalization quinoxalin-2(1H)-ones has been investigated, its difunctionalization, simultaneous construction C-C and N-N bonds directly via reaction, rarely reported. Moreover, obtained products underwent sequential reactions to access C7-NO2 under mild conditions.

Language: Английский

Citations

25
Electrochemical Nitration with Nitrite DOI Creative Commons

Stephan P. Blum,

Christean Nickel,

Lukas Schäffer

et al.

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(22), P. 4936 - 4940

Published: Sept. 28, 2021

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve versatile building blocks. This study represents the electrochemical aromatic with NBu

Language: Английский

Citations

24
Ag/Se‐Catalyzed Selective Epoxidation of β‐Ionone with Molecular Oxygen DOI
Xu Zhang, Tingting Zuo, Lei Yu

et al.

ChemistrySelect, Journal Year: 2022, Volume and Issue: 7(37)

Published: Oct. 5, 2022

Abstract Ag/Se could be easily fabricated by calcining selenium and silver powders. It was found to an efficient catalyst for the selective epoxidation of endocyclic C=C bond β ‐ionone produce epoxide, important organic intermediate in pharmaceutical industry. is notable that reaction can employ molecular oxygen as cheap, clean relatively safe oxidant, no additives such NHPI are required. The green process makes method practical large‐scale application.

Language: Английский

Citations

8
Electrophilic Aromatic Substitution DOI

G. W. Weaver

Organic Reaction Mechanisms/Organic reaction mechanisms, Journal Year: 2023, Volume and Issue: unknown, P. 213 - 255

Published: Jan. 20, 2023

The significance of aromatic and heterocyclic compounds in both industry academia ensures that investigations into new methods electrophilic substitution (EAS) the underlying mechanisms such transformations continue to receive considerable attention. Halogenation continues be an important area investigation EAS, where more than one halogens can introduced have been described. Studies on bromination their much Hydrogen peroxide has used combination with potassium bromide brominate porphyrins a biphasic system. New mechanistic insights iodination presented. use anthraquinone presence TFA as photocatalyst allows visible-light-promoted electron-rich arenas. Recent research classic ever nitration reaction includes computational studies greener, environmentally friendly methods.

Language: Английский

Citations

2
Recent Advances in Functionalization of Aromatic C(sp2)—H Bonds Based on N-Nitroso Direction DOI
Fang Wang, Lei Wang

Chinese Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 43(12), P. 4157 - 4157

Published: Jan. 1, 2023

Language: Английский

Citations

2
Photocatalytic aerobic oxidative deoximation reaction with degradable rhodamine B DOI
Feng Wang,

Rongrong Qian,

Lei Yu

et al.

Reaction Chemistry & Engineering, Journal Year: 2022, Volume and Issue: 8(4), P. 849 - 854

Published: Dec. 22, 2022

Photocatalytic aerobic oxidative deoximation with rhodamine B affords a new method for organic synthesis. Compared reported works, the photosensitizer was cheap and degradable, while substrate scope of reaction wide.

Language: Английский

Citations

3
Nucleophilic Aromatic Substitution DOI

M. R. Crampton

Organic Reaction Mechanisms/Organic reaction mechanisms, Journal Year: 2023, Volume and Issue: unknown, P. 179 - 211

Published: Jan. 20, 2023

A chlorogermabenzene has been generated by reaction of an aluminacyclohexadiene with germanium chloride. The cyanodemethoxylation arenes accomplished using a highly oxidizing acridinium photoredox catalyst acetone cyanohydrin as the source cyanide. Arenediazonium triflates have synthesized diazotization anilines t -butylnitrite in presence trifluoromethanesulfonic acid. detection 2,4,6-trinitrotoluene remains active area research, most methods relying on its interaction amino groups. Likely modes include Meisenheimer complex formation and anion transfer methyl proton. It shown that 1,2-azaborine, boron–nitrogen equivalent ortho -benzyne, super-electrophilic boron centre will form adducts xenon carbon monoxides under matrix isolation conditions. Nucleophilic attack chlorine ions benzyne gives anions may be trapped dioxide to ortho-chlorobenzoate ion.

Language: Английский

Citations

0
Oxidation and Reduction DOI

R. N. Mehrotra

Organic Reaction Mechanisms/Organic reaction mechanisms, Journal Year: 2023, Volume and Issue: unknown, P. 65 - 140

Published: Jan. 20, 2023

A total of 24 reviews including 6 mini and 4 accounts are published in 2019. The first the describes processing polysaccharides, particularly recalcitrant insoluble such as cellulose lignocellulosic biomass, by lytic polysaccharide monooxygenases (LPMOs), a monocopper enzyme. LPMO reactions driven both molecular oxygen hydrogen peroxide. application an azo-phenolate ligand-coordinated nickel catalyst N-alkylation variety anilines alcohols is reported. redox-active azo ligand stores generated during alcohol oxidation redelivers it to situ imine leading amine. simple efficient protocol for regioselective indoles 2-oxindoles using sulfuric acid adsorbed on silica gel reagent reaction has broad substrate scope functional group tolerance.

Language: Английский

Citations

0
Nitration of N -acetyl anilides using silver(I) nitrate/persulfate combination DOI

Hathaichanok Sanjeam,

Chutima Kuhakarn,

Pawaret Leowanawat

et al.

Synthetic Communications, Journal Year: 2022, Volume and Issue: 52(9-10), P. 1279 - 1289

Published: May 19, 2022

Nitration of N-acetyl anilides using a simple combination AgNO3 and K2S2O8 as stable nitro source an oxidant, respectively, was explored. The reaction practical to operate proceeded under considerably mild conditions (reflux in acetonitrile) within acceptable time (6 h). para-substituted gave only ortho-nitrated products moderate good yields (30–63% yields). ortho-, meta-, or non-substituted mixture nitrated (30–72% combined yields) with preferentially at the para- over ortho-position (ortho:para; 1.0:1.1–1.0:2.8).

Language: Английский

Citations

0