Ni(acac)2-catalyzed cross-coupling and carbonylative cross-coupling of organostannanes with hypervalent iodonium salts

ABSTRACT. The free fatty acid receptor 4 (FFA4 or GPR120) has appeared as an interesting potential target for the treatment of metabolic disorders. At present, most FFA4 ligands are carboxylic acids that are assumed to mimic the endogenous long-chain fatty acid agonists. Here, we report preliminary structure-activity relationship studies of a previously disclosed non-acidic sulfonamide FFA4 agonist. Mutagenesis studies indicate that the compounds are orthosteric agonists despite the absence of a carboxylate function. The preferred compounds showed full agonist activity on FFA4 and complete selectivity over FFA1, although a significant fraction of these non-carboxylic acids also showed partial antagonistic activity on FFA1. Studies in normal and diet-induced obese (DIO) mice with the preferred compound 34 showed improved glucose tolerance after oral dosing in an oral glucose tolerance test. Chronic dosing of 34 in DIO mice resulted in significantly increased insulin sensitivity and a moderate but significant reduction in bodyweight, effects that were also present in mice lacking FFA1 but absent in mice lacking FFA4.

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“…37 Ligand conformational sampling was performed using default settings. Prime was used to refine residues within 5.0 Å of ligand poses.…”

Section: -(3-chloro-5-(pyridin-2-yloxy)phenyl)-23-dihydrobenzo[d]ismentioning

confidence: 99%

Non-Acidic Free Fatty Acid Receptor 4 Agonists with Antidiabetic Activity

et al. 2016

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“…Coordination to metal centers not only can stabilize otherwise unstable organic fragments, but also can deeply modify their reactivity. 13,14 The mechanism of the present reaction (scheme 1) initially proceeds through the coordination of the nitrogen and oxygen of the C=O group with nickel acetylacetonate or Lewis acidic sites on montmorillonite K-10. Then methine carbon of β-enamino compounds attack to electrophile.…”

Section: Methodsmentioning

confidence: 99%

“…In this study, all the products were characterized by melting point, IR, 1 H and 13 C NMR spectral data, as well as by their elemental analysis. The results obtained demonstrate that Ni(acac) 2 is a good catalyst that allows the formation of a new carbon-carbon bond between β-enamino compounds with phenyl isocyanate and phenyl isothiocyanate.…”

Section: Methodsmentioning

confidence: 99%

Nickel acetylacetonate [Ni(acac)2] and montmorillonite K-10 promoted regioselective C-acylation of β-enamino compounds

Sheibani¹,

Seifi²

2009

Arkivoc

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“…[114] Nickel-katalysierte Arylierungen und carbonylierende Arylierungen von Aryl-und Alkinylstannanen wurden ebenfalls beschrieben. [115] Suzuki-Kreuzkupplungen mit Arylboronsäuren können mit 0.2 Mol-% [Pd(PPh 3 ) 4 ] bei Raumtemperatur ausgeführt werden, wobei die Biarylprodukte nach nur 5 min in 87-99 % Ausbeute erhalten wurden. [116] Auch Tetraarylborate sind für diese Umsetzung geeignet und liefern die Biarylprodukte nach nur 20 s unter Mikrowellenbestrahlung.…”

Section: B Olofsson Und E a Merrittunclassified

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

2009

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Die jüngsten bahnbrechenden Entwicklungen bei der Anwendung von Diaryliodoniumsalzen in Kreuzkupplungsreaktionen haben diese ehemals unterentwickelte Klasse von Reagentien in die vorderste Reihe der organischen Chemie katapultiert. Mit dem Aufkommen neuartiger, einfacher, effizienter Methoden zur Synthese dieser Reagentien lassen sich noch sehr viel mehr Einsatzmöglichkeiten voraussehen. Wir bieten hier einen Überblick über die historischen und neuerlichen Fortschritte bei der Synthese und Anwendung von Diaryliodoniumsalzen.

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Ni(acac)2-catalyzed cross-coupling and carbonylative cross-coupling of organostannanes with hypervalent iodonium salts

Cited by 35 publications

References 12 publications

Non-Acidic Free Fatty Acid Receptor 4 Agonists with Antidiabetic Activity

Non-Acidic Free Fatty Acid Receptor 4 Agonists with Antidiabetic Activity

Nickel acetylacetonate [Ni(acac)2] and montmorillonite K-10 promoted regioselective C-acylation of β-enamino compounds

Diaryliodoniumsalze – aus dem Nichts ins Rampenlicht

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