- Copper-free sonogashira coupling reaction using a trans-spanning 1,2-Bis(2-thienylethynyl)benzene ligand
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Novel copper-free Sonogashira coupling reaction of aryl halides with terminal acetylenes proceeded in the presence of 1,2-bis(2-thienylethynyl) benzene (1) as a trans-bidentatable ligand.
- Atobe, Shingo,Sonoda, Motohiro,Suzuki, Yuki,Shinohara, Hiroyuki,Yamamoto, Takuya,Ogawa, Akiya
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- Coupling of thiols and aromatic halides promoted by diboron derived super electron donors
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We have proven that pyridine-boryl complexes can be used as superelectron donors to promote the coupling of thiols and aromatic halides through a SRN1 mechanism. The reaction is efficient for a broad substrate scope, tolerating heterocycles including pyridines, enolizable or reducible functional groups. The method has been applied to intermediates in drug synthesis as well as interesting functionalized polythioethers through a controlled and consecutive intramolecular electron transfer process.
- Franco, Mario,Vargas, Emily L.,Tortosa, Mariola,Cid
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supporting information
p. 11653 - 11656
(2021/11/12)
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- Electrochemical Thiolation and Borylation of Arylazo Sulfones with Thiols and B2pin2
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An efficient electrochemical synthesis approach of various unsymmetrical thioethers and arylboronates has been developed. Bench stable arylazo sulfones were used as radical precursors for carbon-heteroatom bond formation under electrochemical conditions. Moreover, the scalability of this approach was evaluated by performing the electrochemical thiolation and borylation of arylazo sulfones with thiols and B2pin2 on a gram scale. This protocol not only avoided the use of stoichiometric oxidants, metal catalysts, activating agents and even added bases, but also exhibited favorable functional group tolerance. (Figure presented.).
- Wang, Rongkang,Chen, Fangming,Jiang, Lvqi,Yi, Wenbin
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supporting information
p. 1904 - 1911
(2021/02/12)
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- AROMATIC SULFIDE COMPOUNDS AND METHODS AND USE THEREOF
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Described herein, inter alia, are aromatic sulfide compositions and methods for treating or preventing cancer using the same.
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Paragraph 0169; 0185
(2015/11/03)
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- Palladium Nanoparticles Immobilized on Nanosilica Triazine Dendritic Polymer (Pd np -nSTDP) as Catalyst in the Synthesis of Mono-, Di-, and Trisulfides through C-S Cross-Coupling Reactions
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A wide variety of diaryl sulfides has been synthesized in excellent yields via C-S cross-couplings of aryl/heteroaryl halides with aromatic/heteroaromatic thiols in the presence of palladium nanoparticles immobilized on nanosilica triazine dendritic polymer (Pd np -nSTDP) as a reusable catalyst under thermal conditions and microwave irradiation. Pd np -nSTDP also showed excellent catalytic activity for the preparation of a series of di- and trisulfides with benzene, pyridine, pyrimidine, and/or 1,3,5-triazine as the central cores by one-pot multi C-S cross-coupling reactions. Georg Thieme Verlag Stuttgart. New York.
- Isfahani, Amir Landarani,Mohammadpoor-Baltork, Iraj,Mirkhani, Valiollah,Moghadam, Majid,Khosropour, Ahmad Reza,Tangestaninejad, Shahram,Nasr-Esfahani, Mahboobeh,Rudbari, Hadi Amiri
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supporting information
p. 645 - 652
(2014/04/03)
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- Diaryl and heteroaryl sulfides: Synthesis via sulfenyl chlorides and evaluation as selective anti-breast-cancer agents
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A mild protocol for the synthesis of diaryl and heteroaryl sulfides is described. In a one-pot procedure, thiols are converted to sulfenyl chlorides and reacted with arylzinc reagents. This method tolerates functional groups including aryl fluorides and chlorides, ketones, as well as N-heterocycles including pyrimidines, imidazoles, tetrazoles, and oxadiazoles. Two compounds synthesized by this method exhibited selective activity against the MCF-7 breast cancer cell line in the micromolar range.
- Yonova, Ivelina M.,Osborne, Charlotte A.,Morrissette, Naomi S.,Jarvo, Elizabeth R.
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p. 1947 - 1953
(2014/04/03)
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- C - S coupling using a mixed-ligand Pd catalyst: A highly effective strategy for synthesizing arylthio-substituted heterocycles
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C - S coupling: A variety of arylthio-substituted heterocycles can be prepared through C - S coupling of the corresponding halide-substituted heterocycles by using a mixed-ligand palladium catalyst, [Pd2(dba) 3]/ Xantphos/CyPF-tBu (see scheme; dba=dibenzylideneacetone). This catalytic system is extremely powerful and efficient, allowing even C - Cl bond activation.
- Cong, Mei,Fan, Yuting,Raimundo, Jean-Manuel,Xia, Yi,Liu, Yang,Quelever, Gilles,Qu, Fanqi,Peng, Ling
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supporting information
p. 17267 - 17272
(2014/01/06)
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- Antimycobacterial Agents. 1. Thio Analogues of Purine
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Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 μg/mL respectively against the Mtb H37Rv strain. N9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.
- Pathak, Ashish K.,Pathak, Vibha,Seitz, Lainne E.,Suling, William J.,Reynolds, Robert C.
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p. 273 - 276
(2007/10/03)
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- Synthesis of alkylthio- and arylthioheteroarenes by regioselective grignard reaction of thiocyanatoheteroarenes
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Treatment of thiocyanatoheteroarenes (1) with Grignard reagents (2) afforded alkylthio- or arylthioheteroarenes (3-6) in good yields. Grignard reagents regioselectively attacked the sulfur atom of the thiocyanato group owing to the metal-chelating effect of this group in combination with the hetero ring-nitrogen. 2-Thiocyanatopyridine (1a), 2-thiocyanatopyrimidine (1b), 2-thiocyanatobenzothiazole (1c), and 4-thiocyanatoquinazoline (1d) were converted into a variety of sulfides. Sulfides consisting of two heteroarenes linked by a sulfur atom were readily obtained by this method.
- Nagasaki, Izuru,Matsumoto, Miyuki,Yamashita, Masanori,Miyashita, Akira
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p. 1015 - 1024
(2007/10/03)
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