- Temperature Controlled Selective C-S or C-C Bond Formation: Photocatalytic Sulfonylation versus Arylation of Unactivated Heterocycles Utilizing Aryl Sulfonyl Chlorides
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A visible-light-induced photocatalytic method for the arylsulfonylation of heterocycles has been developed. The synthetic utility of this reaction is reflected by the direct use of commercially available sulfonyl chlorides and heterocycles under room temperature conditions. Complementarily, the photocatalytic arylation of heterocycles by sulfonyl chlorides via extrusion of SO2 is feasible at elevated temperature conditions, allowing switching between arylation or arylsulfonylation with excellent chemoselectivity.
- Pagire, Santosh K.,Hossain, Asik,Reiser, Oliver
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- Determination of the inhibitory effects of N-methylpyrrole derivatives on glutathione reductase enzyme
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Glutathione reductase (GR) is a crucial antioxidant enzyme which is responsible for the maintenance of antioxidant GSH molecule. Antimalarial effects of some chemical molecules are attributed to their inhibition of GR, thus inhibitors of this enzyme are expected to be promising candidates for the treatment of malaria. In this work, GR inhibitory properties of N-Methylpyrrole derivatives are reported. It was found that all compounds have better inhibitory activity than the strong GR inhibitor N,N-bis(2-chloroethyl)-N-nitrosourea, especially three molecules, 8 m, 8?n, and 8?q, were determined to be the most powerful among them. Findings of our study indicates that these Schiff base derivatives are strong GR inhibitors which can be used as leads for designation of novel antimalarial candidates.
- Kocao?lu, Esma,Talaz, Oktay,?avdar, Hüseyin,?entürk, Murat,Supuran, Claudiu T.,Ekinci, Deniz
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- A case of chain propagation: α-aminoalkyl radicals as initiators for aryl radical chemistry
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The generation of aryl radicals from the corresponding halides by redox chemistry is generally considered a difficult task due to their highly negative reduction potentials. Here we demonstrate that α-aminoalkyl radicals can be used as both initiators and chain-carriers for the radical coupling of aryl halides with pyrrole derivatives, a transformation often employed to evaluate new highly reducing photocatalysts. This mode of reactivity obviates for the use of strong reducing species and was also competent in the formation of sp2 C-P bonds. Mechanistic studies have delineated some of the key features operating that trigger aryl radical generation and also propagate the chain process.
- Constantin, Timothée,Juliá, Fabio,Leonori, Daniele,Sheikh, Nadeem S.
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- Generation of Aryl Radicals from Aryl Halides: Rongalite-Promoted Transition-Metal-Free Arylation
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A new and practical method for the generation of aryl radicals from aryl halides is reported. Rongalite as a novel precursor of super electron donors was used to initiate a series of electron-catalyzed reactions under mild conditions. These transition-metal-free radical chain reactions enable the efficient formation of C-C, C-S, and C-P bonds through homolytic aromatic substitution or SRN1 reactions. Moreover, the synthesis of antipsychotic drug Quetiapine was performed on gram scale through the described method. This protocol demonstrated its potential as a promising arylation method in organic synthesis.
- Yu, Fazhi,Mao, Runyu,Yu, Mingcheng,Gu, Xianfeng,Wang, Yonghui
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p. 9946 - 9956
(2019/09/04)
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- C–H Arylation of N-Heteroarenes under Metal-Free Conditions and its Application towards the Synthesis of Pentabromo- and Pentachloropseudilins
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Herein, we are reporting metal-free conditions for radical initiation and direct C–H arylation of N-heteroarenes. Starting from aniline, the corresponding arenediazonium salt generated in situ is reduced to an aryl radical in the presence of chloropromazine hydrochloride, a new reagent for this application. The optimized procedures are mild, operationally simple, and are working successfully with more diverse substrates in comparison to reported methods. The optimized method is also employed for the synthesis of marine natural products Pentabromo- and Pentachloropseudilins (PBP/PCP). In the present study, we also validated the potential of the Pentachloropseudilin (PCP), thus synthesized, for inhibition of Myosin1 function in mammalian cells and confirmed that PCP phenocopies Myosin1c depletion in cells.
- Kumar, Mukesh,Sharma, Shweta,Sil, Parijat,Kushwaha, Manoj,Mayor, Satyajit,Vishwakarma, Ram A.,Singh, Parvinder Pal
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supporting information
p. 3591 - 3598
(2019/06/20)
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- Palladium-catalysed direct desulfitative arylation of pyrroles using benzenesulfonyl chlorides as alternative coupling partners
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The reactivity of pyrrole derivatives for palladium-catalysed desulfitative arylation has been investigated. 1-Methyl-, 1-phenyl- and 1-benzylpyrroles were successfully coupled with a variety of benzenesulfonyl chlorides using a phosphine-free catalyst. Highly regioselective arylations at carbon C2 of pyrroles were observed in all cases. A wide variety of substituents on the benzenesulfonyl derivative was tolerated. It should be noted that even bromo- and iodo-benzenesulfonyl chlorides were successfully coupled with pyrrole derivatives without cleavage of the C-Br or C-I bonds, allowing further transformations. Surprisingly, with indoles, mixtures of C2- and C3-arylation products were obtained.
- Jin, Rongwei,Yuan, Kedong,Chatelain, Emmanuelle,Soul, Jean-Franois,Douceta, Henri
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p. 3831 - 3841
(2015/01/16)
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- Room-temperature arylation of arenes and heteroarenes with diaryliodonium salts by photoredox catalysis
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Aryl radicals produced by irradiation of diaryliodonium salts with visible light under the catalysis of [Ru(bpy)3]2+ undergo coupling with a wide range of arenes and heteroarenes, affording various biaryls through direct C-H arylation at room temperature. Georg Thieme Verlag Stuttgart · New York.
- Liu, Yu-Xia,Xue, Dong,Wang, Jia-Di,Zhao, Cong-Jun,Zou, Qing-Zhu,Wang, Chao,Xiao, Jianliang
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supporting information
p. 507 - 513
(2013/04/10)
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