92866-00-7Relevant academic research and scientific papers
Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3
Tummatorn, Jumreang,Punjajom, Kunlayanee,Rodphon, Warabhorn,Ruengsangtongkul, Sureeporn,Chaisan, Nattawadee,Lumyong, Kanyapat,Thongsornkleeb, Charnsak,Nimnual, Phongprapan,Ruchirawat, Somsak
supporting information, p. 4694 - 4697 (2019/06/27)
1,1-Disubstituted vinyl triflates are synthesized by direct hydrotriflation of terminal alkynes employing a combination of TfOH and TMSN3 in DCM at room temperature. Interestingly, under these conditions, only terminal alkynes were selectively
Zinc-Catalysed Hydroboration of Terminal and Internal Alkynes
Mandal, Souvik,Mandal, Sayantan,Geetharani
supporting information, p. 4553 - 4556 (2019/08/20)
A regioselective hydroboration of alkynes has been developed by using commercially available zinc triflate as a catalyst, in the presence of catalytic amount of NaBHEt3. The reaction tolerates a wide range of terminal alkynes having several synthetically useful functional groups and proceeds regioselectively to furnish hydroborated products in moderate to excellent yields. This system shows moderate chemoselectivity towards terminal C≡C bond over terminal and internal C=C bond and internal C≡C bond.
Nickel-Catalyzed Highly Regioselective Hydrocyanation of Terminal Alkynes with Zn(CN)2 Using Water as the Hydrogen Source
Zhang, Xingjie,Xie, Xin,Liu, Yuanhong
, p. 7385 - 7389 (2018/06/11)
The first efficient and general nickel-catalyzed hydrocyanation of terminal alkynes with Zn(CN)2 in the presence of water has been developed. The reaction provides a regioselective protocol for the synthesis of functionalized vinyl nitriles with a range of structural diversity under mild reaction conditions while obviating use of the volatile and hazardous reagent of HCN. Deuterium-labeling experiments confirmed the role of water as the hydrogen source in this hydrocyanation reaction.
Synthesis of plasmodione metabolites and 13C-enriched plasmodione as chemical tools for drug metabolism investigation
Feng, Liwen,Lanfranchi, Don Antoine,Cotos, Leandro,Cesar-Rodo, Elena,Ehrhardt, Katharina,Goetz, Alice-Anne,Zimmermann, Herbert,Fenaille, Fran?ois,Blandin, Stephanie A.,Davioud-Charvet, Elisabeth
, p. 2647 - 2665 (2018/04/27)
Malaria is a tropical parasitic disease threatening populations in tropical and sub-tropical areas. Resistance to antimalarial drugs has spread all over the world in the past 50 years, thus new drugs are urgently needed. Plasmodione (benzylmenadione series) has been identified as a potent antimalarial early lead drug, acting through a redox bioactivation on asexual and young sexual blood stages. To investigate its metabolism, a series of plasmodione-based tools, including a fully 13C-labelled lead drug and putative metabolites, have been designed and synthesized for drug metabolism investigation. Furthermore, with the help of UHPLC-MS/MS, two of the drug metabolites have been identified from urine of drug-treated mice.
A one-pot method for the synthesis of phenylalkynyl-substituted terminal alkynes by deprotection/stannylation followed by a Migita-Kosugi-Stille coupling
Peng, Li-Fen,Wang, Bing-Hao,Wang, Ming,Tang, Zi-Long,Jiang, Yan-Zi,Jiao, Yin-Chun,Xu, Xin-Hua
, p. 235 - 238 (2018/06/27)
A practical one-pot approach for the synthesis of arylalkynyl-substituted terminal alkynes has been developed through a deprotection/ stannylation of a phenylethynyl phosphine oxide followed by Migita-Kosugi-Stille coupling, avoiding the longer synthetic route involving repeated deprotection/Sonogashira coupling. Other features of this approach include mild reaction conditions, excellent yields, facile isolation of products and wide functional group tolerance.
Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group
Tian, Duanshuai,Li, Chengxi,Gu, Guoxian,Peng, Henian,Zhang, Xumu,Tang, Wenjun
supporting information, p. 7176 - 7180 (2018/05/29)
Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral α-aryl-α-mesylated acetamides and arylboronic acids provided access to a series of chiral α,α-diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB1 receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.
MONOMER, POLYMER, COMPENSATION FILM, OPTICAL FILM, AND DISPLAY DEVICE
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, (2017/03/21)
A monomer represented by Chemical Formula 1-1 wherein in Chemical Formula 1-1, Z, L1, L2, R1 to R6, n, m, p, and a to f are the same as defined in the detailed description.
Reversible Hydride Transfer to N,N′-Diarylimidazolinium Cations from Hydrogen Catalyzed by Transition Metal Complexes Mimicking the Reaction of [Fe]-Hydrogenase
Hatazawa, Masahiro,Yoshie, Naoko,Seino, Hidetake
, p. 8087 - 8099 (2017/07/22)
[Fe]-hydrogenase is a key enzyme involved in methanogenesis and facilitates reversible hydride transfer from H2 to N5,N10-methenyltetrahydromethanopterin (CH-H4MPT+). In this study, a reaction system was developed to model the enzymatic function of [Fe]-hydrogenase by using N,N′-diphenylimidazolinium cation (1+) as a structurally related alternative to CH-H4MPT+. In connection with the enzymatic mechanism via heterolytic cleavage of H2 at the single metal active site, several transition metal complex catalysts capable of such activation were utilized in the model system. Reduction of 1[BF4] to N,N′-diphenylimidazolidine (2) was achieved under 1 atm H2 at ambient temperature in the presence of an equimolar amount of NEt3 as a proton acceptor. The proposed catalytic pathways involved the generation of active hydride complexes and subsequent intermolecular hydride transfer to 1+. The reverse reaction was accomplished by treatment of 2 with HNMe2Ph+ as the proton source, where [(ν5-C5Me5)Ir{(p-MeC6H4SO2)NCHPhCHPhNH}] was found to catalyze the formation of 1+ and H2 with high efficiency. These results are consistent with the fact that use of 2,6-lutidine in the forward reaction or 2,6-lutidinium in the reverse reaction resulted in incomplete conversion. By combining these reactions using the above Ir amido catalyst, the reversible hydride transfer interconverting 1+/H2 and 2/H+ was performed successfully. This system demonstrated the hydride-accepting and hydride-donating modes of biologically relevant N-heterocycles coupled with proton concentration. The influence of substituents on the forward and reverse reactivities was examined for the derivatives of 1+ and 2 bearing one para-substituted N-phenyl group.
Molecular daisy chains: Synthesis and aggregation studies of an amphiphilic molecular rod
Rotzler, Juergen,Drayss, Sylvie,Hampe, Oliver,Haeussinger, Daniel,Mayor, Marcel
supporting information, p. 2089 - 2101 (2013/04/10)
A water-soluble cyclophane as the loop subunit, monofunctionalized with a molecular rod, has been synthesized to introduce a new binding motif for mechanically interlinked oligomers. It has been demonstrated that this hermaphroditic compound forms [c2]dai
One-pot transformation of Ph2P(O)-protected ethynes: Deprotection followed by transition metal-catalyzed coupling
Peng, Lifen,Xu, Feng,Suzuma, Yoshinori,Orita, Akihiro,Otera, Junzo
, p. 12802 - 12808 (2014/01/17)
Ph2P(O)-protected ethynes were successfully transformed to arylethynes in one-pot manner through t-BuOK-catalyzed deprotection followed by Sonogashira coupling with aryl halide. The arylethynes were obtained similarly by Ph2P(O)-deprotection, stannylation of the resulting terminal ethynes, and Migita-Kosugi-Stille coupling. Deprotection followed by intramolecular Eglinton coupling could be carried out in one-pot to provide cyclic butadiynes.
