Published TCIMAIL newest issue No.196
Maximum quantity allowed is 999
CAS RN: 808142-88-3 | Produkte #: B6258
(4,4'-Di-tert-butyl-2,2'-bipyridine-κ2N1,N1')[bis[5-fluoro-2-(5-methyl-2-pyridinyl-κN)phenyl-κC1]]iridium Hexafluorophosphate
Reinheit: >90.0%(HPLC)
- (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(4-fluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate
- [Ir(p-F(Me)ppy)2-(4,4'-dtbbpy)]PF6
Einheit | Stückpreis | Belgien | Japan* | Menge |
---|---|---|---|---|
200MG |
131,00 €
|
Kontaktieren Sie uns | 19 |
|
1G |
444,00 €
|
2 | 24 |
|
*In Belgien verfügbare Lagerbestände werden in 1 bis 3 Tagen geliefert.
*In Japan verfügbare Lagerbestände werden in 1 bis 2 Wochen geliefert. (unter Ausschluss von regulierten Artikeln und Trockeneislieferungen).
Artikel # | B6258 |
Reinheit / Analysenmethode | >90.0%(HPLC) |
Summenformel / Molekülmasse | C__4__2H__4__2F__8IrN__4P = 978.00 |
Physikalischer Zustand (20 °C) | Solid |
Lagerungstemperatur | Room Temperature (Recommended in a cool and dark place, <15°C) |
Unter Inertgas lagern | Store under inert gas |
Zu vermeidende Bedingungen | Light Sensitive,Air Sensitive |
CAS RN | 808142-88-3 |
Reaxys Registrierungsnummer | 17851242 |
PubChem-Stoff-ID | 468591004 |
MDL-Nummer | MFCD31707653 |
Appearance | Light yellow to Yellow powder to crystal |
Purity(HPLC) | min. 90.0 area% |
NMR | confirm to structure |
Piktogramm | |
Signalwort | Achtung |
Gefahrenhinweise | H315 : Verursacht Hautreizungen. H319 : Verursacht schwere Augenreizung. |
Sicherheitshinweise | P264 : Nach Gebrauch Haut gründlich waschen. P280 : Schutzhandschuhe/ Augenschutz/ Gesichtsschutz tragen. P302 + P352 : BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser waschen. P337 + P313 : Bei anhaltender Augenreizung: Ärztlichen Rat einholen/ ärztliche Hilfe hinzuziehen. P362 + P364 : Kontaminierte Kleidung ausziehen und vor erneutem Tragen waschen. P332 + P313 : Bei Hautreizung: Ärztlichen Rat einholen/ ärztliche Hilfe hinzuziehen. |
HS-Nr. (Import / Export) (TCI-E) | 2843909000 |
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Used Chemicals
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- 2-Methyl-4-phenyl-2-butanol [M0398]
- Oxalyl Chloride [O0082]
- (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(2',4'-difluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate (= [Ir(p-F(Me)ppy)2-(4,4'-dtbbpy)]PF6) [B6254]
- N-Fluoro-N'-(chloromethyl)triethylenediamine Bis(tetrafluoroborate) (= F-TEDA-BF4) [F0358]
- Disodium Hydrogenphosphate Dodecahydrate
- Diethyl Ether
- Acetone
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Procedure
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A 4-neck round bottom flask was charged with 2-methyl-4-phenyl-2-butanol (5 g, 30 mmol, 1 eq) and diethyl ether (300 mL, 0.1 mol/L). The solution was cooled under 5 ˚C, then oxalyl chloride (7.78 g, 60 mmol, 2 eq) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 6 h. After the reaction, the reaction mixture was cooled under 5 ˚C and quenched with ion-exchanged water (55 mL). The solution was transferred into a separatory funnel, and the aqueous layer was extracted with diethyl ether (30 mL, twice). The combined organic layers were washed with brine, dried over sodium sulfate (50 g) for about 30 minutes and then filtered. The solvent was removed in vacuo, giving compound 1 as a light yellow oil (4.91 g, y. 68.3%), which was used without further purification.
1 (1.3 g, 5.5 mmol, 1.0 eq), disodium hydrogenphosphate, dodecahydrate (3.9 g, 11 mmol, 2.0 eq), F-TEDA-BF4 (3.3 g, 9.3 mmol, 1.7 eq), [Ir(p-F(Me)ppy)2-(4,4'-dtbbpy)]PF6 (0.053 g, 0.05 mmol, 0.94 mol%) were dissolved in acetone (44 mL) and of ion-exchanged water (11 mL) at rt under N2. The reaction mixture was degassed with nitrogen for 15 minutes before irradiation. The mixture was placed at a distance of 2-3 cm from Blue LED lamp with a cooling fan. The reaction mixture was stirred at rt under visible light irradiation until 1 was completely consumed. After 6 h of irradiation, the reaction mixture was diluted with diethyl ether (50 mL) and ion-exchanged water (50 mL). The solution was transferred to a separatory funnel, and the aqueous layer was extracted with diethyl ether (30 mL, twice). The combined organic layers were washed with brine, dried over sodium sulfate (50 g) for about 30 minutes and then filtered. The solvent was removed in vacuo, giving crude as a blown oil (0.96 g). The crude was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1, Rf = 0.75) to give compound 2 as a colorless oil (0.394 g, y. 43%)
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Experimenter’s Comments
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- Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40W×2.
- The reaction mixture was cooled to rt with a cooling fan.
- The reaction mixture was monitored by 1H NMR and GCMS.
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Analytical Data
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Compound 2
1H NMR (400 MHz, CDCl3); δ 7.32-7.27 (m, 2H), 7.20 (d, J = 7.8 Hz, 3H), 2.75-2.71 (m, 2H), 1.97-1.88 (m, 2H), 1.41 (d, J = 21.5 Hz, 6H).
13C NMR (101 MHz, CDCl3); δ 142.01, 128.42, 128.28, 125.85, 95.33 (d, JC,F = 165.0 Hz), 43.32 (d, JC,F = 22.9 Hz), 30.24 (d, JC,F = 4.8 Hz), 26.67 (d, JC,F = 24.8 Hz).
19F NMR (376 MHz, CDCl3); δ -139.87 (m, 1F).
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Lead Reference
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- Photoredox-catalyzed deoxyfluorination of activated alcohols with Selectfluor🄬
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Other References
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- Direct, enantioselective α-alkylation of aldehydes using simple olefins
- Decarboxylative sp3 C–N coupling via dual copper and photoredox catalysis
Artikel / Broschüren
[TCI Practical Example] The Deoxyfluorination of Alcohol Using a Photoredox Catalyst
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