Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

Tao, Yu; Guo, Mingqing; Wen, Simiaomiao; Zhao, Rongrong; Wang, Jinlong; Sun, Yanli; Liu, Qixing

doi:10.1039/d1ra02007b

Cited by 12 publications

(4 citation statements)

References 48 publications

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“…The reaction of 1a did not proceed in the absence of the decatungstate catalyst (Table , entry 9). Because the direct photo-oxidation of 1o with molecular oxygen gives benzophenone, we carried out the reaction in the absence of a photocatalyst under black light irradiation, which gave a low yield of benzophenone 2o (13%) (Table , entry 10).…”

mentioning

confidence: 99%

Photocatalytic Oxidative Cleavage of Alkenes by Molecular Oxygen: Reaction Scope, Mechanistic Insights, and Flow Application

Shih

Hyodo

et al. 2022

J. Org. Chem.

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The oxidative cleavage of C�C bonds with molecular oxygen was promoted effectively by a catalytic amount of a decatungstate photocatalyst using black light irradiation (365 nm). Not only aromatic ketones but also aliphatic ketones were obtained by the photocatalytic protocol. The continuous flow reaction of α-methylstyrene using a highpower ultraviolet light-emitting diode (365 nm) dramatically decreased the reaction time.

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confidence: 99%

Photocatalytic Oxidative Cleavage of Alkenes by Molecular Oxygen: Reaction Scope, Mechanistic Insights, and Flow Application

Shih

Hyodo

et al. 2022

J. Org. Chem.

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“… 9H-xanthen-9-one ( 4p ) [ 72 ]: Grayish white solid (88 mg, 90%); 1 H NMR (400 MHz, DMSO- d6 ) δ 8.35 (dd, J = 8.0, 1.6 Hz, 2H), 7.73 (td, J = 7.6, 1.6 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H), 7.40–7.36 (m, 2H); 13 C NMR (101 MHz, DMSO- d6 ) δ 177.2, 156.1, 134.8, 126.7, 123.9, 121.8, 118.0. 9H-thioxanthen-9-one ( 4q ) [ 73 ]: Light yellow solid (93 mg, 88%); 1 H NMR (400 MHz, DMSO- d6 ) δ 8.62 (dd, J = 8.0, 1.2 Hz, 2H), 7.65–7.57 (m, 4H), 7.51–7.47 (m, 2H); 13 C NMR (101 MHz, DMSO- d6 ) δ 180.0, 137.3, 132.3, 129.9, 129.2, 126.3, 126.0. methyl 2-(1-(4-acetylbenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetate ( 4r ) [ 44 ]: Grayish white solid (148 mg, 78%); 1 H NMR (400 MHz, DMSO- d6 ) δ 8.06 (d, J = 8.4 Hz, 2H), 7.79 (d, J = 8.4 Hz, 2H), 6.96 (d, J = 2.4 Hz, 1H), 6.85 (d, J = 9.2 Hz, 1H), 6.65 (dd, J = 9.2, 2.4 Hz, 1H), 3.83 (s, 3H), 3.71 (s, 3H), 3.67 (s, 2H), 2.68 (s, 3H), 2.36 (s, 3H); 13 C NMR (101 MHz, DMSO- d6 ) δ 197.3, 171.3, 168.5, 156.2, 139.8, 139.6, 135.9, 130.8, 130.7, 129.7, 128.6, 115.1, 112.9, 111.7, 101.4, 55.7, 52.2, 30.1, 26.9, 13.5.…”

Section: Methodsmentioning

confidence: 99%

“…9H-thioxanthen-9-one ( 4q ) [ 73 ]: Light yellow solid (93 mg, 88%); 1 H NMR (400 MHz, DMSO- d6 ) δ 8.62 (dd, J = 8.0, 1.2 Hz, 2H), 7.65–7.57 (m, 4H), 7.51–7.47 (m, 2H); 13 C NMR (101 MHz, DMSO- d6 ) δ 180.0, 137.3, 132.3, 129.9, 129.2, 126.3, 126.0.…”

Section: Methodsmentioning

confidence: 99%

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

Luo

et al. 2023

Molecules

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We present an environment-friendly and highly efficient method for the oxidation of aromatic alcohols to carboxylic acids or ketones in air via light irradiation under external catalyst-, additive-, and base-free conditions. The photoreaction system exhibits a wide substrate scope and the potential for large-scale applications. Most of the desired products are easily obtained via recrystallization and separation from low-boiling reaction medium acetone in good yields, and the products can be subsequent directly transformed without further purification.

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“…Emodin is known for its anti-oxidant, anti-ulcerogenic, antibacterial, anti-fibrotic, anti-inflammatory, anti-cardiovascular, anti-viral and anti-cancer activities [14][15][16][17][18][19]. It has demonstrated antitumor activity against various cancers such as leukemia, squamous cell carcinoma of human tongue, lung cancer, gallbladder cancer, breast cancer, colon cancer and others [9,14,15,20,21]. Modified emodin compounds have therefore shown relevant pharmacological activity [22][23][24][25][26][27].…”

Section: Introductionmentioning

confidence: 99%

Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63

et al. 2021

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The current COVID-19 outbreak has highlighted the need for the development of new vaccines and drugs to combat Severe Acute Respiratory Syndrome-Coronavirus-2 (SARS-CoV-2). Recently, various drugs have been proposed as potentially effective against COVID-19, such as remdesivir, infliximab and imatinib. Natural plants have been used as an alternative source of drugs for thousands of years, and some of them are effective for the treatment of various viral diseases. Emodin (1,3,8-trihydroxy-6-methylanthracene-9,10-dione) is a biologically active anthraquinone with antiviral activity that is found in various plants. We studied the selectivity of electrophilic aromatic substitution reactions on an emodin core (halogenation, nitration and sulfonation), which resulted in a library of emodin derivatives. The main aim of this work was to carry out an initial evaluation of the potential to improve the activity of emodin against human coronavirus NL63 (HCoV-NL63) and also to generate a set of initial SAR guidelines. We have prepared emodin derivatives which displayed significant anti-HCoV-NL63 activity. We observed that halogenation of emodin can improve its antiviral activity. The most active compound in this study was the iodinated emodin analogue E_3I, whose anti-HCoV-NL63 activity was comparable to that of remdesivir. Evaluation of the emodin analogues also revealed some unwanted toxicity to Vero cells. Since new synthetic routes are now available that allow modification of the emodin structure, it is reasonable to expect that analogues with significantly improved anti-HCoV-NL63 activity and lowered toxicity may thus be generated.

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Poly(ethylene glycol) dimethyl ether mediated oxidative scission of aromatic olefins to carbonyl compounds by molecular oxygen

Abstract: A simple and practical O2 oxidized scission of monosubstituted, gem- and 1,2-disubstituted, trisubstituted and tetrasubstituted aromatic olefins to aldehydes and ketones in PEGDME has been developed.

Cited by 12 publications

References 48 publications

Photocatalytic Oxidative Cleavage of Alkenes by Molecular Oxygen: Reaction Scope, Mechanistic Insights, and Flow Application

Photocatalytic Oxidative Cleavage of Alkenes by Molecular Oxygen: Reaction Scope, Mechanistic Insights, and Flow Application

External Catalyst- and Additive-Free Photo-Oxidation of Aromatic Alcohols to Carboxylic Acids or Ketones Using Air/O2

Antiviral Activities of Halogenated Emodin Derivatives against Human Coronavirus NL63

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