- Promoting charge separation in donor-acceptor conjugated microporous polymers: Via cyanation for the photocatalytic reductive dehalogenation of chlorides
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Conjugated microporous polymers (CMPs) have emerged as promising heterogeneous photocatalysts for organic transformations owing to their structural designability and functional versatility. However, limited by the insufficient separation of the photo-generated excitons, their photocatalytic efficiency falls far short of expectations. Herein, we demonstrate a cyanation strategy to promote charge carrier separation in CMPs by selectively incorporating carbazole and cyano groups as electron-donating and electron-withdrawing units, respectively. The resulting CMPs feature π-extended donor (D)-acceptor (A) conjugation structures endowing them with distinct semiconducting properties, in which the efficient charge separation and transfer and wide visible-light absorption are facilitated. Compared to the cyano-free counterpart, the cyano-functionalized CMPs showed superior photocatalytic efficiency as exemplified by photocatalytic reductive dehalogenation of chlorides. More prominently, full recyclability of the designed CMPs as well as catalytic activity for at least ten runs without the loss of catalytic performance in photocatalytic reductive dehalogenation of chlorides demonstrated their robustness and sustainability. This journal is
- Deng, Jiyong,Fang, Zhengjun,Lan, Donghui,Liao, Yunfeng,Liu, Qingquan,Zhang, Weijie,Zhou, Xiang
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p. 7151 - 7159
(2021/11/17)
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- Photoinduced Acetylation of Anilines under Aqueous and Catalyst-Free Conditions
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A green and efficient visible-light induced functionalization of anilines under mild conditions has been reported. Utilizing nontoxic, cost-effective, and water-soluble diacetyl as photosensitizer and acetylating reagent, and water as the solvent, a variety of anilines were converted into the corresponding aryl ketones, iodides, and bromides. With advantages of environmentally friendly conditions, simple operation, broad substrate scope, and functional group tolerance, this reaction represents a valuable method in organic synthesis.
- Yang, Yu-Ming,Yan, Wei,Hu, Han-Wei,Luo, Yimin,Tang, Zhen-Yu,Luo, Zhuangzhu
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p. 12344 - 12353
(2021/09/02)
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- V2O5@TiO2 Catalyzed Green and Selective Oxidation of Alcohols, Alkylbenzenes and Styrenes to Carbonyls
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The versatile application of different functional groups such as alcohols (1° and 2°), alkyl arenes, and (aryl)olefins to construct carbon-oxygen bond via oxidation is an area of intense research. Here, we report a reusable heterogeneous V2O5@TiO2 catalyzed selective oxidation of various functionalities utilizing different mild and eco-compatible oxidants under greener reaction conditions. The method was successfully applied for the alcohol oxidation, oxidative scission of styrenes, and benzylic C?H oxidation to their corresponding aldehydes and ketones. The utilization of mild and eco-friendly oxidizing reagents such as K2S2O8, H2O2 (30 % aq.), TBHP (70 % aq.), broad substrate scope, gram-scale synthesis, and catalyst recyclability are notable features of the developed protocol.
- Upadhyay, Rahul,Kumar, Shashi,Maurya, Sushil K.
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p. 3594 - 3600
(2021/07/02)
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- Rate enhancements due to ultrasound in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic compounds in presence of KHSO4/KCl
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Chlorination of aromatic compounds underwent magnificent rate accelerations in isoquinolinium dichromate and isoquinolinium chlorochromate catalyzed chlorination of aromatic hydrocarbons in the presence of KCl and KHSO4. Reaction times reduced highly significantly from 4-5 h in conventional protocol to 30-40 min under sonication, followed by high yields of monochloro derivatives as products with high regioselectivity.
- Rajanna,Rao, A. Sambashiva,Chakravarthi,Reddy, K. Rajendar
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p. 167 - 170
(2017/12/26)
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- Design, synthesis and structure-based optimization of novel isoxazole-containing benzamide derivatives as FtsZ modulators
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Antibiotic resistance among clinically significant bacterial pathogens is becoming a prevalent threat to public health, and new antibacterial agents with novel mechanisms of action hence are in an urgent need. Utilizing computational docking method and structure-based optimization strategy, we rationally designed and synthesized two series of isoxazol-3-yl- and isoxazol-5-yl-containing benzamide derivatives that targeted the bacterial cell division protein FtsZ. Evaluation of their activity against a panel of Gram-positive and -negative pathogens revealed that compounds B14 and B16 that possessed the isoxazol-5-yl group showed strong antibacterial activity against various testing strains, including methicillin-resistant Staphylococcus aureus and penicillin-resistant S. aureus. Further molecular biological studies and docking analyses proved that the compound functioned as an effective inhibitor to alter the dynamics of FtsZ self-polymerization via a stimulatory mechanism, which finally terminated the cell division and caused cell death. Taken together, these results could suggest a promising chemotype for development of new FtsZ-targeting bactericidal agent.
- Bi, Fangchao,Song, Di,Zhang, Nan,Liu, Zhiyang,Gu, Xinjie,Hu, Chaoyu,Cai, Xiaokang,Venter, Henrietta,Ma, Shutao
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- Biomimetic Oxidative Deamination Catalysis via ortho-Naphthoquinone-Catalyzed Aerobic Oxidation Strategy
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An ortho-naphthoquinone-catalyzed oxidative deamination reaction has been developed where the molecular oxygen and water serve as the sole oxidant and nucleophile. The current aerobic deamination reaction proceeds via the ketimine formation between ortho-naphthoquinones and amines followed by the prototropic rearrangement and hydrolysis by water, representing a biomimetic oxidative deamination of amine species in the human body by the liver and kidneys. The compatibility of ortho-naphthoquinone organocatalysts with molecular oxygen and water opens up a new biomimetic catalyst system that can function as versatile deaminases for a variety of amine-containing molecules such as amino acids and DNA nuclear bases.
- Golime, Gangadhararao,Bogonda, Ganganna,Kim, Hun Young,Oh, Kyungsoo
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p. 4986 - 4990
(2018/05/14)
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- Acceptorless dehydrogenation and dehydrogenative coupling of alcohols catalysed by protic NHC ruthenium complexes
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A new family of protic NHC Ru complexes ligated with a phosphine-tethered imidazole moiety were prepared, which can act as excellent catalysts for acceptorless dehydrogenation of secondary alcohols and dehydrogenative coupling of primary and secondary alcohols, thus leading to the formation of a variety of carbonyl compounds with release of H2.
- Chang, Weihong,Gong, Xue,Wang, Shuizhong,Xiao, Ling-Ping,Song, Guoyong
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supporting information
p. 3466 - 3471
(2017/04/26)
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- Metal-Free Markovnikov-Type Alkyne Hydration under Mild Conditions
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A Markovnikov-type alkyne hydration protocol is presented using 20% CF3SO3H (TfOH) as the catalyst under unprecedented mild conditions applicable to various alkynes, including terminal arylalkynes, terminal nonfunctionalized aliphatic alkynes, and internal alkynes with excellent regioselectivity in good to excellent yields (average yields >85%). The reaction procedure operates under mild conditions (25-70°C), with broad functional group compatibility, and uses only slightly more than a stoichiometric amount of water in the absence of any transition metal. The success of this protocol hinges upon the utilization of trifluoroethanol as the solvent.
- Liu, Wenbo,Wang, Haining,Li, Chao-Jun
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supporting information
p. 2184 - 2187
(2016/06/01)
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- An environmentally benign hydration of alkynes catalyzed by gallic acid/tannic acid in water
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A gallic acid catalyzed hydration strategy from alkynes under mild conditions has been developed. The catalyst system exhibits excellent activity, thus avoiding the use of any transition metal, strong acids or other toxic reagent as cocatalysts. Recycling experiments were conducted, and this procedure can be scaled up. Other tannins such as tannic acid can also be applied in this reaction which shows the potential utilization of natural feedstocks.
- Deng, Tao,Wang, Cheng-Zhang
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p. 7029 - 7032
(2016/10/07)
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- Design, synthesis and pharmacology of 1,1-bistrifluoromethylcarbinol derivatives as liver X receptor β-selective agonists
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A novel series of 1,3-bistrifluoromethylcarbinol derivatives that act as liver X receptor (LXR) β-selective agonists was discovered. Structure-activity relationship studies led to the identification of molecule 62, which was more effective (Emax) and selective toward LXRβ than T0901317 and GW3965. Furthermore, 62 decreased LDL-C without elevating the plasma TG level and significantly suppressed the lipid-accumulation area in the aortic arch in a Bio F1B hamster fed a diet high in fat and cholesterol. We demonstrated that our LXRβ agonist would be potentially useful as a hypolipidemic and anti-atherosclerotic agent. In this manuscript, we report the design, synthesis and pharmacology of 1,3-bistrifluoromethylcarbinol derivatives.
- Koura, Minoru,Matsuda, Takayuki,Okuda, Ayumu,Watanabe, Yuichiro,Yamaguchi, Yuki,Kurobuchi, Sayaka,Matsumoto, Yuuki,Shibuya, Kimiyuki
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p. 2668 - 2674
(2015/06/08)
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- Palladium catalyzed decarboxylative acylation of arylboronic acid with ethyl cyanoacetate as a new acylating agent: Synthesis of alkyl aryl ketones
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Palladium catalyzed acylation of arylboronic acid containing various functional groups was performed efficiently by ethyl cyanoacetate/substituted ethyl cyanoacetate as the acylating agent in aqueous triflic acid medium. The alkyl aryl ketones were obtained in good to excellent yields, first by addition of arylboronic acid to the nitrile group of ethyl cyanoacetate and their derivatives, followed by in situ decarboxylation of the resulting β-ketoester.
- Yousuf, Md,Das, Tuluma,Adhikari, Susanta
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p. 8763 - 8770
(2015/11/10)
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- Biomimetic self-assembling acylphthalocyanines
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We synthesized a series of biomimetic self-assembling phthalocyanines equipped with carbonyl groups as recognition motifs, a central zinc atom and diverse solubilizing alkyl chains mimicking for the first time with these robust pigments the natural chloro
- Jin, Hong-Guang,Balaban, Mihaela Carmen,Chevallier-Michaud, Sabine,Righezza, Michel,Balaban, Teodor Silviu
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supporting information
p. 11884 - 11887
(2015/07/20)
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- Tetra-n-butylammonium bromide: A simple but efficient organocatalyst for alcohol oxidation under mild conditions
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A simple but efficient organocatalytic system with 5 mol% tetra-n-butylammonium bromide (TBAB) as the catalyst has been identified for alcohol oxidation for the first time. This organocatalytic system is compatible with a broad range of benzylic/allylic alcohols with various catalytically reactive groups. Besides, it shows excellent selectivity for secondary benzylic alcohols over aliphatic alcohols, and good selectivity over the primary benzylic alcohol site in 4-(1-hydroxyethyl)benzyl alcohol. Thus, the features of simplicity, high efficiency, selectivity and mildness of reaction conditions associated with this TBAB organocatalytic system suggest its potential for widespread use in synthetic chemistry.
- Ma, Xinyi,Li, Zhongfeng,Liu, Feijie,Cao, Shengli,Rao, Honghua
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supporting information
p. 1741 - 1746
(2014/06/09)
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- Aerobic oxidation of alcohols under mild conditions catalyzed by novel polymer-incarcerated, carbon-stabilized gold nanoclusters
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Polymer-incarcerated, carbon-stabilized gold nanoclusters were found to be highly active in heterogeneous catalysis for the oxidation of secondary alcohols using molecular oxygen in aqueous medium. After optimization of catalyst preparation methods, highly loaded and highly effective catalysts were obtained, and a broad range of secondary alcohols could be oxidized by using these catalysts under mild conditions. The catalysts could be recovered and reused several times without significant loss of activity. Moreover, kinetics of the oxidation reaction with (±)-1-phenylethanol was investigated.
- Lucchesi, Celine,Inasaki, Takeshi,Miyamura, Hiroyuki,Matsubara, Ryosuke,Kobayashi, Shu
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supporting information; experimental part
p. 1996 - 2000
(2009/07/25)
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- 2-Hydroxymethyl-4-[5-(4-methoxyphenyl)-3-trifluoromethyl-1H-1-pyrazolyl] -1-benzenesulfonamide (DRF-4367): An orally active COX-2 inhibitor identified through pharmacophoric modulation
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Analogs of 1,5-diarylpyrazoles with a novel pharmacophore at N1 were designed, synthesized and evaluated for the in-vitro cyclooxygenase (COX-1/COX-2) inhibitory activity. The variations at/around position-4 of the C-5 phenyl ring in conjunction with a CF3 and CHF2 groups at C-3 exhibited a high degree of potency and selectivity index (SI) for COX-2 inhibition. The in-vivo evaluation of these potent compounds with a few earlier ones indicated the 4-OMe-phenyl analog 6 and the 4-NHMe-phenyl analog 9 with a CF3, and the 4-OEt-phenyl analog 19 with a CHF2 group at C-3 to possess superior potency than celecoxib. In addition to its impressive anti-inflammatory, antipyretic, analgesic and anti-arthritic properties, compound 6 (DRF-4367) was found to possess an excellent pharmacokinetic profile, gastrointestinal (GI) safety in the long-term arthritis study and COX-2 potency in human whole blood assay. Thus, compound 6 was selected as an orally active anti-inflammatory candidate for pre-clinical evaluation.
- Singh, Sunil Kumar,Vobbalareddy, Saibaba,Kalleda, Srinivasa Rao,Rajjak, Shaikh Abdul,Casturi, Seshagiri Rao,Datla, Srinivasa Raju,Mamidi, Rao N.V.S.,Mullangi, Ramesh,Bhamidipati, Ravikanth,Ramanujam, Rajagopalan,Akella, Venkateswarlu,Yeleswarapu, Koteswar Rao
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p. 2442 - 2450
(2007/10/03)
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- Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation
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Zn powder is found to catalyze the Friedel-Crafts acylation of aromatic compounds with acyl halides efficiently under microwave irradiation in solvent-free conditions. Activated substrates undergo acylation predominantly at the para-position. The Zn powder can be re-used up to six times after simple washing with diethyl ether and dilute HCl.
- Paul, Satya,Nanda, Puja,Gupta, Rajive,Loupy, Andre
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p. 2877 - 2881
(2007/10/03)
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- N-(α-alkylbenzylidene)-α-phenylalkylamine, its use and process for producing the same and process for producing intermediate therefor
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There is disclosed an N-(α-alkylbenzylidene)-α-phenylalkylamine represented by the general formula (1): STR1 wherein R1 represents a lower alkyl group, R2 represents a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group and X represents a halogen atom or a lower alkoxy group, its use and a process for producing the same and processes for producing intermediates therefor.
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- Bisphosphonic acid derivatives as anti-arthritic agents
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The bisphosphonates of formula (III) bicyclic bisphosphonates (V), and cyclic bisphosphonates (VII) are useful as anti-arthritic agents and do not have the side effects of anti-arthritic agents which are prostaglandin synthetase inhibitors.
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- Crystal Structure and Photochemistry of Four α-Cycloalkyl-p-chloroacetophenones
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The photochemical fragmentation or cyclization reactions of α-cycloalkylacetophenones have been studied by crystal-structure analyses of four chloro derivatives with varying cycloalkyl-ring sizes, and by correlation of crystal- and molecular-structure par
- Evans, Stephen V.,Trotter, James
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- Production of halo-substituted derivatives of acetophenone
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A process for producing halosubstituted derivatives of acetophenone from the respective halocumenes, the term "halo" as used herein, signifying chlorine or bromine, the molecule containing 1 to 3 nuclear halo substituents in the meta- and/or paraposition relative to the isopropyl group. The process comprises oxidizing the halocumene by means of air or oxygen. The oxidation is effected in the presence of a metal phthalocyanine complex as catalyst, and in a most preferred embodiment, in the co-presence of a dichlorobenzene solvent. The preferred halocumenes are p-chlorocumene and p-bromocumene.
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