872273-36-4Relevant academic research and scientific papers
MODULATORS OF THE INTEGRATED STRESS PATHWAY
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Page/Page column 597, (2019/05/22)
Provided herein are compounds, compositions, and methods useful for the modulation of elF2B, for modulating the integrated stress response (ISR) and for treating related diseases; disorders and conditions.
Making the SF5 Group More Accessible: A Gas-Reagent-Free Approach to Aryl Tetrafluoro-λ6-sulfanyl Chlorides
Pitts, Cody Ross,Bornemann, Dustin,Liebing, Phil,Santschi, Nico,Togni, Antonio
supporting information, p. 1950 - 1954 (2019/01/25)
Modern pentafluorosulfanyl (SF5) chemistry has an Achilles heel: synthetic accessibility. Herein, we present the first approach to aryl-SF4Cl compounds (key intermediates in state-of-the-art aryl-SF5 synthesis) that overco
A novel dual-nano assisted synthesis of symmetrical disulfides from aryl/alkyl halides
Devi, Namita,Hazarika, Sukanya,Gogoi, Prasanta,Barman, Pranjit
, p. 1927 - 1938 (2018/07/21)
Here, we have reported a novel approach towards dual-nano assisted synthesis of disulfides from coupling of alkyl/aryl halides and sulfur nanoparticles. The indium oxide nanoparticles as catalyst expedite the conversion and sulfur nanoparticle notably enhances the miscibility, providing a faster, high yielding and cost-effective process in ethanol-water system. The method has synthetic advantages in terms of mild reaction framework, catalyst regeneration, and absence of any sulfide or polysulfide linkage as by-product leading to a column free synthesis. A variety of alkyl, aryl and heteroaryl symmetrical disulfides are obtained in good to excellent yields up to exceeding 98%.
Ni/Ir-Catalyzed Photoredox Decarboxylative Coupling of S-Substituted Thiolactic Acids with Heteroaryl Bromides: Short Synthesis of Sulfoxaflor and Its SF5 Analog
Kanishchev, Oleksandr S.,Dolbier, William R.
supporting information, p. 7677 - 7681 (2017/06/06)
Metallaphotoredox cross-coupling reactions have recently emerged as a powerful tool for the construction of C(sp2)?C(sp3) bonds between alkyl chains and aromatic systems, including electron-deficient heteroaryls, which are known to be challenging coupling partners. In this article, we disclose the Ni/Ir-catalyzed photoredox decarboxylative coupling of readily available S-substituted thiolactic acids with electron-deficient heteroaryl bromides, which resulted in the formation of simple but otherwise not easily accessible heteroarenes with alkylsulfide side chains. To demonstrate a practical use of this coupling reaction, we have shown its efficiency in the one-step synthesis of a key intermediate in the synthesis of the recently marketed insecticide Sulfoxaflor, and for the short synthesis of SF5-Sulfoxaflor.
SF5-Pyridylaryl-λ3-iodonium salts and their utility as electrophilic reagents to access SF5-pyridine derivatives in the late-stage of synthesis
Das, Prajwalita,Takada, Masahiro,Matsuzaki, Kohei,Saito, Norimichi,Shibata, Norio
supporting information, p. 3850 - 3853 (2017/04/06)
Electrophilic pentafluorosulfanyl (SF5) heteroarylation of target molecules using novel reagents is described. Unsymmetrical diaryliodonium reagents 1 having 2-SF5-pyridine have been synthesized in good yields. They are efficient electrophilic reagents for carbon and heterocentered nucleophiles, producing the corresponding SF5-pyridine derivatives in good to excellent yields.
IF5 affects the final stage of the Cl-F exchange fluorination in the synthesis of pentafluoro-λ6-sulfanyl-pyridines, pyrimidines and benzenes with electron-withdrawing substituents
Cui, Benqiang,Kosobokov, Mikhail,Matsuzaki, Kohei,Tokunaga, Etsuko,Shibata, Norio
supporting information, p. 5997 - 6000 (2017/07/10)
A difficult chlorine-fluorine (Cl-F) exchange fluorination reaction in the final stage of the preparation of pentafluoro-λ6-sulfanyl-(hetero)arenes having electron-withdrawing substituents has now been elucidated through the use of iodine pentafluoride. A major side-reaction of C-S bond cleavage was sufficiently inhibited by the potential interaction between F and I with a halogen bonding.
Silver-induced self-immolative Cl-F exchange fluorination of arylsulfur chlorotetrafluorides: Synthesis of arylsulfur pentafluorides
Cui, Benqiang,Jia, Shichong,Tokunaga, Etsuko,Saito, Norimichi,Shibata, Norio
supporting information, p. 12738 - 12741 (2017/12/06)
A novel strategy for the synthesis of arylsulfur pentafluorides by silver carbonate-induced Cl-F exchange fluorination of arylsulfur chlorotetrafluorides is reported. This fluorination does not require any exogenous fluoride sources. Rather, the reaction proceeds via the self-immolation of the substrate Ar-SF4Cl.
Organocatalytic visible light induced S-S bond formation for oxidative coupling of thiols to disulfides
Tankam, Theeranon,Poochampa, Kamolrut,Vilaivan, Tirayut,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 788 - 793 (2016/01/20)
In this work, we developed a visible light induced oxidative coupling of thiols into the corresponding disulfides in a process catalyzed by an inexpensive and non hazardous Rose Bengal dye. Our optimization study revealed that the use of Rose Bengal catal
Synthesis and characterization of 2-pyridylsulfur pentafluorides
Kanishchev, Oleksandr S.,Dolbier, William R.
supporting information, p. 280 - 284 (2015/04/21)
Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2' -dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.
Hypervalent iodine(III)-promoted metal-free S-H activation: An approach for the construction of S-S, S-N, and S-C bonds
Rattanangkool, Eakkaphon,Krailat, Watanya,Vilaivan, Tirayut,Phuwapraisirisan, Preecha,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 4795 - 4804 (2014/08/05)
The activation of the sulfur atom of thiols with (diacetoxyiodo)benzene (DIB) has been explored in the preparation of symmetrical disulfides and sulfenamides. Disulfides can be produced in excellent yields (75-95%) upon treatment of thiols with DIB. The reaction was complete in less than five minutes at room temperature. Aliphatic, aromatic, and heteroaromatic thiols are compatible with this transformation. Moreover, heteroaromatic disulfides obtained from heteroaromatic thiols further reacted with a nucleophilic amine in the presence of a base to provide the corresponding sulfenamides in fair to good yields (43-90%) in a one-pot fashion. The methodology was successfully extended to indole as a representative electron-rich aromatic compound, which allowed successful construction of a S-C bond in one pot. The key benefits of this reaction include lower toxicity, low cost of DIB reagent, and mild reaction conditions (room temperature, undried solvents and open flask).
