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1. De novo synthesis of Cr-embedded MOF-199 and derived porous CuO/CuCr₂O₄ composites for enhanced phenol hydroxylation

Author:
Huang, Yu-Yuan; Konnerth, Hannelore; Yeh, Jyun-Yi; Prechtl, Martin H. G.; Wen, Cheng-Yen; Wu, Kevin C.-W.
Source:
Green chemistry 2019 v.21 no.8 pp. 1889-1894
ISSN:
1463-9270
Subject:
phenol,   etc   ; green chemistry; hydroxylation; oxides;     Show all 4 Subjects
Abstract:
... A de novo synthesis of Cr-embedded MOF-199 was developed for the first time. This Cr-MOF-199 material was further derived into CuO/CuCr₂O₄ composites with a porous and uniform structure. The obtained bimetallic oxides with a porous structure were further applied in phenol hydroxylation. ...
DOI:
10.1039/c8gc03348j

2. Recyclable nickel-catalyzed C–H/O–H dual functionalization of phenols with mandelic acids for the synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions

Author:
Tang, Zhi; Tong, Zhou; Xu, Zhihui; Au, Chak-Tong; Qiu, Renhua; Yin, Shuang-Feng
Source:
Green chemistry 2019 v.21 no.8 pp. 2015-2022
ISSN:
1463-9270
Subject:
phenols,   etc   ; antioxidants; catalysts; green chemistry; nickel;     Show all 5 Subjects
Abstract:
... Herein, we developed a protocol for the efficient synthesis of 3-aryl benzofuran-2(3H)-ones under solvent-free conditions from phenols and mandelic acids using Ni(OTf)₂ as a catalyst. A diverse range of mandelic acids and phenols undergo C–H/O–H bond dual functionalization to generate products in moderate to good or excellent yields. The nickel catalyst can be easily recycled in a test of three ru ...
DOI:
10.1039/c9gc00305c

3. Effect of hydroxypropyl-β-cyclodextrin on the cometabolism of phenol and phenanthrene by a novel Chryseobacterium sp.

Author:
Xiao, Meng; Yin, Xiangyang; Gai, Hengjun; Ma, Honglei; Qi, Yanfeng; Li, Kun; Hua, Xia; Sun, Meng; Song, Hongbing
Source:
Bioresource technology 2019 v.273 pp. 56-62
ISSN:
0960-8524
Subject:
phenol,   etc   ; Chryseobacterium; coal; phenanthrenes; solubility; toxicity; wastewater;     Show all 7 Subjects
Abstract:
... Cometabolic degradation is an effective method to remove the polycyclic aromatic hydrocarbons (PAHs) with phenol as growth substrate from coal chemical wastewater (CCW). Unfortunately, the toxicity and low solubility of PAHs always restrict their degradation. In this study, Chryseobacterium sp. H202 was firstly isolated from the aerobic segment of CCW. Then, to improve the cometabolic degradation ...
DOI:
10.1016/j.biortech.2018.10.087

4. Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

Author:
Shen, Zuyuan; Zhang, Shilei; Geng, Huihui; Wang, Jiarui; Zhang, Xinyu; Zhou, Anqi; Yao, Cheng; Chen, Xiaobei; Wang, Wei
Source:
Organic letters 2019 v.21 no.2 pp. 448-452
ISSN:
1523-7052
Subject:
phenols,   etc   ; amines; chemical reactions; cost effectiveness; moieties;     Show all 5 Subjects
Abstract:
... A conceptually novel sulfoxonium metathesis reaction between TMSOI and cost-effective DMSO-d₆ is developed for the efficient generation of a new trideuteromethylation reagent TDMSOI. The new reagent TDMSOI is produced highly efficiently by simply heating a mixture of TMSOI and DMSO-d₆ and directly used for subsequent trideuteromethylation in a “one-pot” operation. The preparative power of the new ...
DOI:
10.1021/acs.orglett.8b03641

5. Synthesis of 2-Aryloxy-1,3-dienes from Phenols and Propargyl Carbonates

Author:
Ishida, Naoki; Hori, Yusaku; Okumura, Shintaro; Murakami, Masahiro
Source:
Journal of the American Chemical Society 2018 v.141 no.1 pp. 84-88
ISSN:
1520-5126
Subject:
phenols,   etc   ; carbonates; moieties; stereoselectivity;     Show all 4 Subjects
Abstract:
... A convenient method for the synthesis of 1,3-dienes from readily available compounds is reported. 2-Aryoxy-1,3-dienes are produced stereoselectively by a nickel-catalyzed reaction of propargyl carbonates with phenols. Functional group tolerance is broad to allow iodo, formyl, and boryl groups. The resulting 1,3-dienes are of much synthetic value because they can participate in a wide variety of re ...
DOI:
10.1021/jacs.8b11159

6. Fabrication of β-phase AgI and Bi2O3 co-decorated Bi2O2CO3 heterojunctions with enhanced photocatalytic performance

Author:
Wang, Qi; Zhang, Chenlu; Wu, Hong; Gao, Qiaoyuan; Duan, Ran; Chen, Chuncheng
Source:
Journal of colloid and interface science 2019 v.547 pp. 1-13
ISSN:
0021-9797
Subject:
phenol,   etc   ; catalysts; chromium; electric current; photocatalysis; surface area; temperature;     Show all 7 Subjects
Abstract:
... Bi2O2CO3 was co-decorated by β-phase AgI and Bi2O3 forming visible-light-active AgI(β)/Bi2O3(β)-Bi2O2CO3 composite via simply calcining AgI/Bi2O2CO3. The calcination temperature and time played vital role in regulating the structure as well as photocatalytic performance. Optimal AgI(β)/Bi2O3(β)-Bi2O2CO3 was obtained after 325 ◦C calcination for 2 h with 5% AgI. The ratio of Bi2O3 to Bi2O2CO3 was e ...
DOI:
10.1016/j.jcis.2019.03.088

7. A general-applicable model for estimating the binding coefficient of organic pollutants with dissolved organic matter

Author:
Li, Yi-Long; He, Wei; Wu, Rui-Lin; Xing, Baoshan; Xu, Fu-Liu
Source:
The Science of the total environment 2019 v.670 pp. 226-235
ISSN:
0048-9697
Subject:
phenols,   etc   ; aquatic environment; dissolved organic matter; models; pollutants; regression analysis;     Show all 6 Subjects
Abstract:
... The binding constant (Kdoc) of organic pollutants (OPs) with dissolved organic matter (DOM) is an important parameter in determining the partitioning of OPs in the aquatic environment. Most estimation models have focused on calculating the Kdoc of a specific group of OPs but failed to obtain Kdoc values of different OPs effectively over the last three decades. In this study, we attempted to build ...
DOI:
10.1016/j.scitotenv.2019.03.146

8. Chemical characterization methods for the analysis of structural extracellular polymeric substances (EPS)

Author:
Felz, Simon; Vermeulen, Pascalle; van Loosdrecht, Mark C.M.; Lin, Yue Mei
Source:
Water research 2019 v.157 pp. 201-208
ISSN:
0043-1354
Subject:
phenol,   etc   ; biofilm; colorimetry; polymers; proteins; sludge; sulfuric acid; uronic acids;     Show all 8 Subjects
Abstract:
... Biofilm structure and functionality depend on extracellular polymeric substances (EPS), but analytical methods for EPS often lack specificity which limits progress of biofilm research.EPS were extracted from aerobic granular sludge and analyzed with frequently applied colorimetric methods. The colorimetric methods were evaluated based on their applicability for EPS analysis. EPS fractions of inter ...
DOI:
10.1016/j.watres.2019.03.068

9. Core/shell structured CdS/polydopamine/TiO2 ternary hybrids as highly active visible-light photocatalysis

Author:
Wang, Minggui; Cui, Zhengxing; Yang, Mang; Lin, Longjie; Chen, Xichang; Wang, Min; Han, Jie
Source:
Journal of colloid and interface science 2019 v.544 pp. 1-7
ISSN:
0021-9797
Subject:
phenol,   etc   ; coatings; dopamine; hydrolysis; nanospheres; photocatalysis; titanium dioxide;     Show all 7 Subjects
Abstract:
... Core/shell structured CdS/polydopamine/TiO2 (CdS/PDA/TiO2) ternary hybrids were fabricated by sequentially coating of PDA and TiO2 on CdS nanospheres through dopamine self-polymerization and TBOT hydrolysis and hydrothermal processes. The reaction rate constants of CdS/PDA/TiO2 ternary hybrids toward the degradation of RhB, MB and phenol were more than 3 times higher than those of CdS/TiO2 hybrids ...
DOI:
10.1016/j.jcis.2019.02.080

10. Preparation of a chemiluminescence sensor for multi-detection of benzimidazoles in meat based on molecularly imprinted polymer

Author:
Cai, Yi; He, Xin; Cui, Peng Lei; Liu, Jing; Li, Zhao Bin; Jia, Bing Jie; Zhang, Teng; Wang, Jian Ping; Yuan, Wan Zhe
Source:
Food chemistry 2019 v.280 pp. 103-109
ISSN:
0308-8146
Subject:
phenols,   etc   ; beef; benzimidazoles; chemiluminescence; detection limit; haptens; mutton; polymers; screening;     Show all 9 Subjects
Abstract:
... In this study, a molecularly imprinted polymer capable of recognizing 8 benzimidazoles was first synthesized. The computation simulation showed that the shape and size of used template were the main factors influencing its recognition ability. Then the polymer was used as recognition reagent to prepare a chemiluminescence sensor on conventional 96-well microplate. The sample solution and a HRP-lab ...
DOI:
10.1016/j.foodchem.2018.12.052

11. A scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with RSH/ROH

Author:
Li, Yujun; Yang, Qi; Yang, Liquan; Lei, Ning; Zheng, Ke
Source:
Chemical communications 2019 v.55 no.34 pp. 4981-4984
ISSN:
1364-548X
Subject:
phenols,   etc   ; cross-coupling reactions; dehydrogenation; electrochemistry; free radicals; phosphorus; thiols;     Show all 7 Subjects
Abstract:
... A practical, scalable electrochemical dehydrogenative cross-coupling of P(O)H compounds with thiols, phenols and alcohols in both an undivided cell and a continuous-flow setup is disclosed. Its broad substrate scope (>50 examples), good functional-group tolerance and scalability (>10 g) show potential for practical synthesis. A preliminary mechanistic study suggests that the phosphorus radicals ar ...
DOI:
10.1039/c9cc01378d

12. Asymmetric synthesis of multifunctional aryl allyl ethers by nucleophilic catalysis

Author:
Zhao, Shuai; Jin, Lei; Chen, Zhi-Li; Rui, Xue; He, Jia-Yi; Xia, Ran; Chen, Ke; Chen, Xiang-Xiang; Yin, Zi-Jian; Chen, Xin
Source:
RSC advances 2019 v.9 no.20 pp. 11585-11588
ISSN:
2046-2069
Subject:
phenols,   etc   ; Lewis bases; carbonates; catalytic activity; enantioselectivity; ethers;     Show all 6 Subjects
Abstract:
... Asymmetric allylic substitution of Morita–Baylis–Hillman (MBH) carbonates with less-nucleophilic phenols mediated by nucleophilic amine catalysis was successfully developed. A variety of substituted aryl allyl ethers were afforded with moderate to high yields with excellent enantioselectivities. The chiral MBH alcohol could be easily accessed from the corresponding aryl allyl ether. ...
DOI:
10.1039/c9ra00155g

13. Organocatalytic strategy for hydrophenolation of gem-difluoroalkenes

Author:
Orsi, Douglas L.; Yadav, M. Ramu; Altman, Ryan A.
Source:
Tetrahedron 2019
ISSN:
0040-4020
Subject:
phenols,   etc   ; catalysts; catalytic activity; chemical reactions; fluorine; moieties;     Show all 6 Subjects
Abstract:
... Gem-difluoroalkenes are an easily accessed fluorinated functional group, and a useful intermediate for elaborating into more complex fluorinated compounds. Currently, most functionalization reactions of gem-difluoroalkenes, with or without a transition metal-based catalyst system, involve the addition or removal of a fluorine atom to generate trifluorinated or monofluorinated products, respectivel ...
DOI:
10.1016/j.tet.2019.04.016

14. Oxidative phenol-arene and phenol-phenol cross-coupling using periodic acid

Author:
Gao, Peng-Cheng; Chen, Huan; Grigoryants, Vladimir; Zhang, Qiang
Source:
Tetrahedron 2019 v.75 no.13 pp. 2004-2011
ISSN:
0040-4020
Subject:
phenol,   etc   ; ambient temperature; chemical structure; cross-coupling reactions; naphthols;     Show all 5 Subjects
Abstract:
... A simple, metal-free protocol for unsymmetrical biaryl coupling using H5IO6 is reported. H5IO6 was evaluated for a novel application in the oxidative cross-coupling of phenol-arene, phenol-phenol, and phenol-naphthol compounds. In this work, most of the couplings were completed within 30 min at ambient temperature. 30 coupling products were conveniently obtained using only 0.5 equivalent of H5IO6 ...
DOI:
10.1016/j.tet.2019.02.021

15. Nickel-Catalyzed Carboxylation of Aryl and Heteroaryl Fluorosulfates Using Carbon Dioxide

Author:
Ma, Cong; Zhao, Chuan-Qi; Xu, Xue-Tao; Li, Zhao-Ming; Wang, Xiang-Yang; Zhang, Kun; Mei, Tian-Sheng
Source:
Organic letters 2019 v.21 no.7 pp. 2464-2467
ISSN:
1523-7052
Subject:
phenol,   etc   ; aromatic hydrocarbons; carbon dioxide; carboxylation; carboxylic acids; chemical structure;     Show all 6 Subjects
Abstract:
... The development of efficient and practical methods to construct carboxylic acids using CO₂ as a C1 synthon is of great importance. Nickel-catalyzed carboxylation of aryl fluorosulfates and heteroaryl fluorosulfates with CO₂ is described, affording arene carboxylic acids with good to excellent yields under mild conditions. In addition, a one-pot phenol fluorosulfation/carboxylation is developed. ...
DOI:
10.1021/acs.orglett.9b00836

16. A visible light photoredox catalyzed carbon radical-mediated generation of ortho-quinone methides for 2,3-dihydrobenzofuran synthesis

Author:
Zhou, Fan; Cheng, Ying; Liu, Xiao-Peng; Chen, Jia-Rong; Xiao, Wen-Jing
Source:
Chemical communications 2019 v.55 no.21 pp. 3117-3120
ISSN:
1364-548X
Subject:
phenols,   etc   ; carbon; catalytic activity; cyclization reactions; quinones; redox reactions;     Show all 6 Subjects
Abstract:
... A visible light photoredox-catalyzed carbon radical-mediated strategy for in situ formation of ortho-quinone methides from 2-vinyl phenols is described. This strategy enables a multicomponent cyclization reaction of 2-vinyl phenols, Umemoto's reagent, and sulfur ylides, providing access to trifluoromethylated 2,3-dihydrobenzofurans. ...
DOI:
10.1039/c9cc00727j

17. Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors

Author:
Dunås, Petter; Paterson, Andrew J.; Kociok-Köhn, Gabriele; Lewis, Simon E.; Kann, Nina
Source:
ACS sustainable chemistry & engineering 2019 v.7 no.7 pp. 7155-7162
ISSN:
2168-0485
Subject:
phenols,   etc   ; Lewis bases; aromatic hydrocarbons; ethanol; iron; solvents;     Show all 6 Subjects
Abstract:
... Renewable phenols have been investigated as nucleophiles for the addition to a cationic cyclohexadienyl iron carbonyl scaffold. Benign conditions compatible with solvents such as ethanol and water were developed, and for the first time, selective C- or O-addition could be achieved. In addition, a novel atom-economic approach to forming the C-addition products directly from the neutral precursor co ...
DOI:
10.1021/acssuschemeng.9b00127

18. Investigating the reactivity of 9-phenyl-9-borafluorene with NH, OH, PH, and SH bonds

Author:
Laperriere, Leif E.; Yruegas, Sam; Martin, Caleb D.
Source:
Tetrahedron 2019 v.75 no.8 pp. 937-943
ISSN:
0040-4020
Subject:
phenol,   etc   ; aniline; boron; chemical bonding; chemical reactions; chemical structure; oxygen;     Show all 7 Subjects
Abstract:
... The reactions of 9-phenyl-9-borafluorene with NH, PH, OH, and SH containing substrates were investigated. Protodeborylation reactions were observed for phenol, water, aniline, and para-bromothiophenol. In the water reaction, both OH bonds reacted with 9-phenyl-9-borafluorene to furnish the oxygen bridged diborane whereas only one of the NH bonds in aniline reacted. Phenylphosphine coordinated to t ...
DOI:
10.1016/j.tet.2018.12.034

19. Photocatalyst-Free Visible-Light Photoredox Dearomatization of Phenol Derivatives Containing Ketoximes: An Easy Access to Spiropyrrolines

Author:
Han, Yongzhen; Jin, Yunhe; Jiang, Min; Yang, Haijun; Fu, Hua
Source:
Organic letters 2019 v.21 no.6 pp. 1799-1803
ISSN:
1523-7052
Subject:
phenols,   etc   ; ambient temperature; chemical structure; photocatalysts; redox reactions;     Show all 5 Subjects
Abstract:
... A novel and simple visible-light photoredox intramolecular dearomatization of phenol derivatives containing ketoximes leading to spiropyrrolines has been developed. The protocol uses readily available 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as the base and electron-donor, visible light as the light source, and the reaction was performed well at room temperature without need of a photocatalyst. Th ...
DOI:
10.1021/acs.orglett.9b00372

20. Probing Through-Space Polar−π Interactions in 2,6-Diarylphenols

Author:
Bosmans, Vera; Poater, Jordi; Hammink, Roel; Tinnemans, Paul; Bickelhaupt, F. Matthias; Mecinović, Jasmin
Source:
Journal of organic chemistry 2019 v.84 no.6 pp. 3632-3637
ISSN:
1520-6904
Subject:
phenol,   etc   ; acidity; chemical reactions; chemical structure; organic chemistry;     Show all 5 Subjects
Abstract:
... Although it is well established that the acidity of phenol can be fine-tuned with substituents on its aromatic ring via through-bond effects, the role of through-space effects on the acidity of phenols is presently poorly understood. Here, we present integrated experimental and computational studies on substituted 2,6-diarylphenols that demonstrate the essential contribution from through-space OH− ...
DOI:
10.1021/acs.joc.8b03147