1208-88-4Relevant articles and documents
BODIPY-Based Photoacid Generators for Light-Induced Cationic Polymerization
Sambath, Karthik,Wan, Zhaoxiong,Wang, Qi,Chen, Hao,Zhang, Yuanwei
, p. 1208 - 1212 (2020)
Photoacid generators (PAGs) are organic compounds that can generate protons (H+) upon irradiation with certain wavelengths of light. In this work, we designed and synthesized the first BODIPY-based PAGs with D-A and D-?-A conjugation structures and achieved green and red LED light-induced acid generation. By the use of red-light absorbance, red-LED-triggered cationic polymerization was demonstrated as a proof-of-concept application of these PAGs.
Expedient Preparation of Aryllithium and Arylzinc Reagents from Aryl Chlorides Using Lithium 4,4′-Di- tert -Butylbiphenylide and Zinc(II) Chloride
Shen, Zhi-Liang,Sommer, Korbinian,Knochel, Paul
, p. 2617 - 2630 (2015)
We report an efficient method for the preparation of aryllithium and zinc reagents from inexpensive and readily available aryl chlorides by using lithium 4,4′-di-tert-butylbiphenylide (LiDBB) as a lithiation reagent. The resulting organometallic reagents underwent subsequent reactions with a variety of electrophiles, such as an aldehydes, DMF, PhSSO2Ph, TsCN, an aryl halide, or an acid chloride (through Pd-catalyzed cross-coupling). Aryl chlorides bearing substituents, including methoxy, 3,4-methylenedioxy, fluoride, TMS, OTMS, NMe2, acetal, and ketal, were shown to be appropriate substrates. Interestingly, aryl chlorides containing a formyl group could also be used, provided that the formyl group was temporarily converted into an α-amino alkoxide by using the lithium amide of N,N,N′-trimethylethylenediamine (LiTMDA). The presence of a hydroxyl group was also tolerated when it was deprotonated with n-BuLi prior to the addition of LiDBB.
Nucleophilic aromatic substitution reaction of nitroarenes with alkyl- or arylthio groups in dimethyl sulfoxide by means of cesium carbonate
Kondoh, Azusa,Yorimitsu, Hideki,Oshima, Koichiro
, p. 2357 - 2360 (2006)
Treatment of nitroarenes having electron-withdrawing groups at the ortho or para position with alkanethiol in the presence of cesium carbonate in dimethyl sulfoxide at 25°C leads to nucleophilic displacement of the nitro group with the alkylthio group. Cesium carbonate is superior to other bases such as potassium carbonate, sodium carbonate, and triethylamine. The cesium-mediated nucleophilic aromatic substitution reaction provides a mild yet powerful and user-friendly protocol for the synthesis of aryl sulfides.
Modulation of photochemical oxidation of thioethers to sulfoxides or sulfones using an aromatic ketone as the photocatalyst
Zhao, Bin,Hammond, Gerald B.,Xu, Bo
supporting information, (2021/09/13)
We have developed an eco-friendly and chemo-selective photocatalytic synthesis of sulfoxides or sulfones via oxidation of sulfides (thioethers) at ambient temperature using air or O2 as the oxidant. An inexpensive thioxanthone was used as the photocatalyst. Our method offers excellent chemical yields and good functional group tolerance. The hydrogen bonding between hexafluoro-2-propanol (HFIP) and sulfoxides may play an important role in minimizing the over-oxidization of sulfoxides.
Chan-Lam-Type C-S Coupling Reaction by Sodium Aryl Sulfinates and Organoboron Compounds
Lam, Long Yin,Ma, Cong
supporting information, p. 6164 - 6168 (2021/08/16)
A Chan-Lam-Type C-S coupling reaction using sodium aryl sulfinates has been developed to provide diaryl thioethers in up to 92% yields in the presence of a copper catalyst and potassium sulfite. Both electron-rich and electron-poor sodium aryl sulfinates and diverse organoboron compounds were tolerated for the synthesis of aryl and heteroaryl thioethers and dithioethers. The mechanistic study suggested that potassium sulfite was involved in the deoxygenation of sulfinate through a radical process.
A Visible-Light-Harvesting Covalent Organic Framework Bearing Single Nickel Sites as a Highly Efficient Sulfur–Carbon Cross-Coupling Dual Catalyst
Chen, Hui,Liu, Wanlu,Laemont, Andreas,Krishnaraj, Chidharth,Feng, Xiao,Rohman, Fadli,Meledina, Maria,Zhang, Qiqi,Van Deun, Rik,Leus, Karen,Van Der Voort, Pascal
supporting information, p. 10820 - 10827 (2021/04/09)
Covalent Organic Frameworks (COFs) have recently emerged as light-harvesting devices, as well as elegant heterogeneous catalysts. The combination of these two properties into a dual catalyst has not yet been explored. We report a new photosensitive triazine-based COF, decorated with single Ni sites to form a dual catalyst. This crystalline and highly porous catalyst shows excellent catalytic performance in the visible-light-driven catalytic sulfur–carbon cross-coupling reaction. Incorporation of single transition metal sites in a photosensitive COF scaffold with two-component synergistic catalyst in organic transformation is demonstrated for the first time.
Design, synthesis, and biological evaluation of pyrimidine analogs as SecA inhibitors
Bamba, Fante,Jin, Jinshan,Chaudhary, Arpana S.,Tai, Phang C.,Wang, Binghe
, p. 1334 - 1340 (2021/03/19)
SecA, a key component of the bacterial Sec-dependent secretion pathway, is an attractive target for the development of new antimicrobial agents. We have previously reported pyrimidine analogs as SecA inhibitors. Herein, we report an extension of the earlier work in the synthesis and evaluation of a series of 15 5-cyanothiouracil derivatives as SecA inhibitors. All the compounds have been evaluated for their inhibition of SecA ATPase (EcSecAN68) and for their antimicrobial activity against Escherichia coli NR698 (a leaky mutant) and Bacillus anthracis Sterne. Twelve compounds showed IC50 of less than 6.3 μM when tested against EcSecAN68. In antimicrobial studies against E. coli NR698, six compounds showed MIC of 12.5 μM with three being less than 6.3 μM. Against B. anthracis Sterne, three compounds showed MIC of 6.3 μM.
Synthesis and biological evaluation of new 1,2,4-triazolo[1,5-a] pyridine and 1,2,4-triazolo[1,5-a] isoquinolinederivatives bearing diphenyl sulfide moiety as antimicrobial agents
El-Adasy, Abu-Bakr A.,El-Haleem Hussein, Abd M.,Ishak, Esam A.,Hafiz, Ibrahim S.A.,Gawish, Emad H.,Elapasery, Morsy A.,El-Gaby, Mohamed S.A.
, p. 913 - 921 (2021/02/12)
Hydrazone derivative (3) was used as a precursor for the synthesis of novel [1,2,4]triazolo[1,5-a]pyridine derivatives via its reaction with some electrophilic reagents. Treatment of hydrazone derivative (3) with arylidenemalononitriles(4) in the presence of piperidine afforded the 1,2,4-triazolo[1,5-a]pyridine derivatives (7a-d). Ternary condensation of hydrazone (3), aliphatic aldehyde and malononitrile (1:1:1 molar ratio) in the presence of a basic catalyst furnished the novel 1,2,4-triazolo[1,5-a]pyridine derivatives (8a,b). Similarly, cyclization of hydrazone (3) with ethyl α-cyanocinnamates (9) (1:1 molar ratio) yields the corresponding 1,2,4-triazolo[1,5-a]pyridines (10a-c). The hydrazone (3) can be cyclized with appropriate arylazomalononitriles(11) to afford the corresponding 1,2,4-triazolo[1,5-a]pyridines (14a,b). The behavior of fused thiophene derivative (15) towards electron-poor olefins was investigated. It is has been found that, 1,2,4-triazolo[1,5-a]isoquinoline derivative (17) was obtained by treatment of thiophene derivative (15) with dimethyl acetylenedicarboxylate (DMAD). Condensation of compound (15) with N-phenylmalemide furnished pyrrolotriazoloisoquinoline derivative (18). Also, the triazoloisoquinoline derivative (19) was obtained by condensation of compound (15) with chalcone. All the newly synthesized compounds were characterized by analytical and spectral data and evaluated for their antibacterial and antifungal activities in vitro against two Gram-positive bacteria, two Gram negative bacteria as well as two fungi. In general, the newly synthesized compounds showed good antimicrobial activities.
Room temperature nickel-catalyzed cross-coupling of aryl-boronic acids with thiophenols: Synthesis of diarylsulfides
Bhowmik, Amit,Fernandes, Rodney A.,Yadav, Mahesh
, p. 2447 - 2458 (2020/04/15)
A NiCl2/2,2′-bipyridine-catalyzed cross-coupling of thiophenols with arylboronic acids has been developed for the synthesis of symmetric and unsymmetric diarylsulfides at room temperature and in air. This methodology is reliable and offers a mild and easy to operate process for the synthesis of arylthioethers, which are essential compounds with applications in the pharmaceutical and agricultural industries. This method avoids the use of expensive transition metals, such as Pd, Ir or Rh, sophisticated ligands and elevated temperatures. It also has a wide substrate scope (55 examples) and provides products in good to excellent yields (72-93%).
CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 15525 - 15538 (2019/10/19)
In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.
