- Engaging sulfinate salts via Ni/photoredox dual catalysis enables facile Csp2-SO2R coupling
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This report details the development and implementation of a strategy to construct aryl- and heteroaryl sulfones via Ni/photoredox dual catalysis. Using aryl sulfinate salts, the C-S bond can be forged at room temperature under base-free conditions. An array of aryl- and heteroaryl halides are compatible with this approach. The broad tolerance and mild nature of the described reaction could potentially be employed to prepare sulfones with biological relevance (e.g., in bioconjugation, drug substance synthesis, etc.) as demonstrated in the synthesis of drug-like compounds or their precursors. When paired with existing Ni/photoredox chemistry for Csp3-Csp2 cross-coupling, an array of diverse sulfone scaffolds can be readily assembled from bifunctional electrophiles. A mechanistic manifold consistent with experimental and computational data is presented.
- Cabrera-Afonso, María Jesús,Lu, Zhi-Peng,Kelly, Christopher B.,Lang, Simon B.,Dykstra, Ryan,Gutierrez, Osvaldo,Molander, Gary A.
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p. 3186 - 3191
(2018/03/30)
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- Regioselective, Molecular Iodine-Mediated C3 Iodination of Quinolines
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A novel and convenient method has been developed for the regioselective iodination of quinolines at their C3 position under metal-free conditions. Iodinated quinolines, which are popular building blocks in organic and medicinal chemistry, can be prepared in gram quantities and good yields using this method and further derivatized to give increasingly complex compounds. Preliminary mechanistic studies have shown that this reaction most likely occurs via a radical intermediate.
- Sun, Kai,Lv, Yunhe,Wang, Junjie,Sun, Jingjing,Liu, Lulu,Jia, Mingyang,Liu, Xin,Li, Zhenduo,Wang, Xin
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supporting information
p. 4408 - 4411
(2015/09/28)
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- Syntheses, radiolabelings, and in vitro evaluations of fluorinated pet radioligands of 5-HT6 serotoninergic receptors
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The 5-HT6 receptors are potent therapeutic targets for psychiatric and neurological diseases (schizophrenia, Alzheimers disease, etc.). However, with lack of specific radiopharmaceuticals, their pharmacology is still incomplete and their exploration is limited to animal models. In this context, we have designed a fluorinated PET radiotracer, [18F]2FNQ1P, that possesses a high affinity and selectivity for 5-HT6. In vitro PET autoradiographies in rat brain sections with this radiotracer were in accordance with the 5-HT6 distribution pattern.
- Colomb, Julie,Becker, Guillaume,Fieux, Sylvain,Zimmer, Luc,Billard, Thierry
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supporting information
p. 3884 - 3890
(2014/05/20)
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- Palladium-catalyzed synthesis of ammonium sulfinates from aryl halides and a sulfur dioxide surrogate: A gas-and reductant-free process
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Sulfonyl-derived functional groups populate a broad range of useful molecules and materials, and despite a variety of preparative methods being available, processes which introduce the most basic sulfonyl building block, sulfur dioxide, using catalytic methods, are rare. Described herein is a simple reaction system consisting of the sulfur dioxide surrogate DABSO, triethylamine, and a palladium(0) catalyst for effective convertion of a broad range of aryl and heteroaryl halides into the corresponding ammonium sulfinates. Key features of this gas-and reductant-free reaction include the low loadings of palladium (1 mol) and ligand (1.5 mol) which can be employed, and the use of isopropyl alcohol as both a solvent and formal reductant. The ammonium sulfinate products are converted in situ into a variety of sulfonyl-containing functional groups, including sulfones, sulfonyl chlorides, and sulfonamides.
- Emmett, Edward J.,Hayter, Barry R.,Willis, Michael C.
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supporting information
p. 10204 - 10208
(2015/03/31)
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- COMBINATION OF CB2 LIGAND AND PARACETAMOL
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Combination of one or more CB2 modulators and paracetamol are useful of treating conditions which are mediated by the activity of CB2 receptors such as an immune disorder, an inflammatory disorder, pain, rheumatoid arthritis, multiple sclerosis, osteoarthritis, and osteoporosis.
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Page/Page column 190
(2008/12/04)
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- QUINOLINE COMPOUNDS CAPABLE OF BINDING THE CB2 AND/OR THE 5-HT6 RECEPTOR
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The present invention relates to novel quinoline derivatives such as compounds of the formula (I) which possess antagonist potency for the 5-HT6 receptor and/or are capable of selectively modulating the cannabinoid 2 receptor and the use of such compounds or pharmaceutical compositions thereof in the treatment of CNS disorders.
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Page/Page column 29-30
(2008/06/13)
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- 8- (1-PIPERAZINYL)- QUINOLINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CNS DISORDERS
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This invention relates to novel quinoline compounds having pharmacological activity, to processes for their preparation, to compositions containing them and to their use in the treatment of CNS and other disorders.
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Page/Page column 12
(2008/06/13)
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- PIPERAZINYL-QUINOLINE DERIVATIVES USEFUL FOR THE TREATMENT OF CNS DISORDERS
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This invention relates to novel quinoline compounds having pharmacological activity, to processes for their preparation, to compositions containing them and to their use in the treatment of CNS and other disorders.
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Page/Page column 10-11
(2010/02/11)
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- 3-ARYLSULFONYL-QUINOLINES AS 5-HT6 RECEPTOR ANTAGONISTS FOR THE TREATMENT OF CNS DISORDERS
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The present invention relates to novel quinoline derivatives such as compounds of the formula (I) which have antagonist potency for the 5-HT6 receptor and the use of such compounds or pharmaceutical compositions thereof in the treatment of C
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Page/Page column 11
(2008/06/13)
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