Copper-Catalyzed Formal CH Carboxylation of Aromatic Compounds with Carbon Dioxide through Arylaluminum Intermediates

2014 ◽  
Vol 10 (4) ◽  
pp. 1010-1016 ◽  
Author(s):  
Atsushi Ueno ◽  
Masanori Takimoto ◽  
Wylie W. N. O ◽  
Masayoshi Nishiura ◽  
Takao Ikariya ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Aromatic Compounds

Carboxylation of aromatic compounds in a supercritical carbon dioxide medium

2012 ◽  
Vol 6 (7) ◽  
pp. 818-826 ◽  
Author(s):  
A. V. Shlyakhtin ◽  
S. Z. Vatsadze ◽  
D. P. Krut’ko ◽  
D. A. Lemenovskii ◽  
M. V. Zabalov
Keyword(s):  
Carbon Dioxide ◽  
Supercritical Carbon Dioxide ◽  
Aromatic Compounds ◽  
Supercritical Carbon

The degradation of p-toluenesulfonate by a Pseudomonas

1970 ◽  
Vol 16 (5) ◽  
pp. 309-316 ◽  
Author(s):  
D. D. Focht ◽  
F. D. Williams
Keyword(s):  
Carbon Dioxide ◽  
Oxygen Uptake ◽  
Aromatic Compounds ◽  
Carbon Sources ◽  
Sole Source ◽  
Carbon Chain ◽  
Ring Cleavage ◽  
Resting Cells ◽  
Resting Cell ◽  
Complete Mineralization

A Pseudomonas isolated from sewage was adapted to use p-toluenesulfonate as the sole source of both carbon and sulfur. Very few of over 30 aromatic compounds tested were used for growth as sole carbon sources. Significantly, sulfobenzoate, phenolsulfonates, and isomers of cresolsulfonates did not support growth. Respirometry studies with washed, resting cells showed similar results. In both studies, benzenesulfonate was always used more rapidly than p-toluenesulfonate. The degradation of p-toluenesulfonate was shown to be over 90% of the theoretical value required for complete mineralization to carbon dioxide, water, and sulfate. When resting cells were incubated with 35S-p-toluenesulfonate, the ratio of oxygen uptake to 35S-sulfate liberation remained constant during the complete degradation period. Radiochromatographic analysis showed no 35S-aromatic intermediates in resting-cell supernatants at any time. Resting cells previously incubated with 35S-p-toluenesulfonate liberated two 35S-labeled aromatic intermediates upon disruption. Resting cells incubated with 1-14C-p-toluenesulfonate produced labeled 3-methylcatechol, labeled acetate, and unlabeled pyruvate. The labeled intermediate, 3-methylcatechol, was degraded by cell-free extracts to labeled acetate. Hydroxylation, desulfonation, ring cleavage, and subsequent fissions of the carbon chain occurred in that order; all steps but the first were catalyzed by cell-free extracts.

Solvolysis of benzyl phenyl ether in high-temperature aqueous methanol solution under high-pressure carbon dioxide

2021 ◽  
Author(s):  
Kenkichi Taniguchi ◽  
Hidetaka Nanao ◽  
Osamu Sato ◽  
Aritomo Yamaguchi ◽  
Masayuki Shirai
Keyword(s):  
Carbon Dioxide ◽  
High Pressure ◽  
High Temperature ◽  
Aromatic Compounds ◽  
Methanol Solution ◽  
Phenyl Ether ◽  
Aqueous Methanol ◽  
Benzyl Phenyl Ether

Alcoholysis of benzyl phenyl ether to various aromatic compounds was studied in high-temperature aqueous methanol solution under high-pressure carbon dioxide conditions.

Beneficial Effect of TMSCl in the Lewis Acid-Mediated Carboxylation of Aromatic Compounds with Carbon Dioxide.

ChemInform ◽  
2006 ◽  
Vol 37 (47) ◽  
Author(s):  
Koji Nemoto ◽  
Hiroki Yoshida ◽  
Yutaka Suzuki ◽  
Naoya Morohashi ◽  
Tetsutaro Hattori
Keyword(s):  
Carbon Dioxide ◽  
Beneficial Effect ◽  
Lewis Acid ◽  
Aromatic Compounds

scholarly journals Redox-neutral Photocatalytic C-H Carboxylation of Arenes and Styrenes with CO2

2020 ◽  
Author(s):  
Matthias Schmalzbauer ◽  
Thomas D. Svejstrup ◽  
Florian Fricke ◽  
Peter Brandt ◽  
Magnus J. Johansson ◽  
...  
Keyword(s):  
Carbon Dioxide ◽  
Organic Synthesis ◽  
High Throughput ◽  
Electron Affinity ◽  
Aromatic Compounds ◽  
High Throughput Screening ◽  
Computational Analysis ◽  
High Energy ◽  
Radical Anions ◽  
Light Excitation

Carbon dioxide (CO<sub>2</sub>) is an attractive one-carbon (C1) building block in terms of sustainability and abundance. However, its low reactivity limits applications in organic synthesis as typically high-energy reagents are required to drive transformations. Here, we present a redox-neutral C−H carboxylation of arenes and styrenes using a photocatalytic approach. Upon blue-light excitation, the anthrolate anion photocatalyst is able to reduce many aromatic compounds to their corresponding radical anions, which react with CO<sub>2</sub> to afford carboxylic acids. High-throughput screening and computational analysis suggest that a correct balance between electron affinity and nucleophilicity of substrates is essential. This novel methodology enables the carboxylation of numerous aromatic compounds, including many that are not tolerated in classical carboxylation chemistry. Over 50 examples of C−H functionalizations using CO<sub>2</sub> or ketones illustrate a broad applicability. The method opens new opportunities for late-stage C−H carboxylation and valorization of common arenes.

Correlation of solubilities of carbon dioxide in aromatic compounds

1992 ◽  
Vol 73 (1-2) ◽  
pp. 1-25 ◽  
Author(s):  
Jun-Shun Yau ◽  
Fuan-Nan Tsai
Keyword(s):  
Carbon Dioxide ◽  
Aromatic Compounds

scholarly journals The chemistry of flavines and flavoproteins. Photoreduction of flavines by amino acids

1968 ◽  
Vol 109 (2) ◽  
pp. 259-268 ◽  
Author(s):  
G. R. Penzer ◽  
G. K. Radda
Keyword(s):  
Carbon Dioxide ◽  
Amino Acids ◽  
Light Intensity ◽  
Potassium Iodide ◽  
Aromatic Compounds ◽  
Phenylacetic Acid ◽  
Intramolecular Interaction ◽  
Kinetic Scheme ◽  
Dimethyl Sulphoxide ◽  
Triplet States

1. Flavines are photoreduced through their triplet states by amines and amino acids (e.g. EDTA and dl-phenylglycine). The anaerobic photoreduction of FMN and several other flavines with dl-phenylglycine was analysed in terms of a detailed kinetic scheme. 2. The reaction produces equimolar amounts of benzaldehyde, carbon dioxide and reduced flavine. 3. The sensitivity of the rates to substituents in the dl-phenylglycine can be described by a Hammett ρ-value of −1·1. 4. Phenylacetic acid behaves differently from dl-phenylglycine or benzylamine towards a series of flavines. 5. The photoreductions are quenched by several aromatic compounds. From the effects of light-intensity and temperature, and by comparison with potassium iodide quenching, it is concluded that inhibition by the aromatic compounds is not simply a collisional process. 6. FAD reacts more slowly than FMN both in the photoreduction and in dark reduction by NADH. Urea and dimethyl sulphoxide decrease the intramolecular interaction in FAD, but they have no effect on the rate of dark reduction of FAD compared with FMN. In contrast, the photoreduction of FAD is quicker in urea.

Beneficial Effect of TMSCl in the Lewis Acid-mediated Carboxylation of Aromatic Compounds with Carbon Dioxide

2006 ◽  
Vol 35 (7) ◽  
pp. 820-821 ◽  
Author(s):  
Koji Nemoto ◽  
Hiroki Yoshida ◽  
Yutaka Suzuki ◽  
Naoya Morohashi ◽  
Tetsutaro Hattori
Keyword(s):  
Carbon Dioxide ◽  
Beneficial Effect ◽  
Lewis Acid ◽  
Aromatic Compounds

Lewis Acid-Mediated Carboxylation of Fused Aromatic Compounds with Carbon Dioxide

2002 ◽  
Vol 31 (1) ◽  
pp. 102-103 ◽  
Author(s):  
Yutaka Suzuki ◽  
Tetsutaro Hattori ◽  
Tomohiro Okuzawa ◽  
Sotaro Miyano
Keyword(s):  
Carbon Dioxide ◽  
Lewis Acid ◽  
Aromatic Compounds
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