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CAS RN: 1335047-34-1 | Product Number: B6254
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|Purity / Analysis Method||>90.0%(HPLC)|
|Molecular Formula / Molecular Weight||C__4__2H__4__0F__1__0IrN__4P = 1013.98|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Light Sensitive,Air Sensitive|
|Appearance||Light yellow to Yellow powder to crystal|
|Purity(HPLC)||min. 90.0 area%|
|Melting Point||360 °C|
|Hazard Statements||H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
|Precautionary Statements||P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
- 4-Methoxystyrene [M0130]
- (4,4'-Di-tert-butyl-2,2'-bipyridine)bis[2-(2',4'-difluorophenyl)-5-methylpyridine]iridium(III) Hexafluorophosphate (= Ir[dF(Me)(ppy)2(dtbbpy)]PF6) [B6254]
2,4,6-Triisopropylbenzenethiol (0.060 g, 0.25 mmol, 0.5 eq), piperidine (0.050 mL, 0.50 mmol, 1.0 eq), 4-methoxystyrene (0.10 mL, 0.75mmol, 1.5 eq), Ir[dF(Me)(ppy)2(dtbbpy)]PF6 (10 mg, 0.0099 mmol, 2.0 mol%) were dissolved in toluene (10 mL) at rt under N2. The mixture was placed at a distance of 2-3 cm from Blue LED lamp with a cooling fan. The yellow orange suspension was stirred at rt under visible light irradiation until the amine was completely consumed. After 12 h of irradiation, the reaction mixture was diluted with ethyl acetate (20 mL) and extracted with 1 mol/L HCl aq. (70 mL x 2). The combined aqueous layer was washed with diethyl ether (30 mL x 2), then neutralized with 2 mol/L NaOH aq. (78 mL) to pH 7 and then saturated sodium bicarbonate aq. (10 mL) was added to ensure slightly basic conditions. The aqueous layer was extracted with dichloromethane (50 mL x 3). The combined organic layer was dried over sodium sulfate (30 g) for about 30 minutes and then filtered. The solvent was removed in vacuo to give compound 1 as a colorless oil (39 mg, y. 35%).
Toluene was degassed with nitrogen for 30 minutes before use.
Irradiation of visible light was performed with Kessil A160WE Tuna Blue 40Wx2.
The reaction mixture was maintained at rt by a cooling fan.
The reaction mixture was monitored by 1H NMR and GC.
1H NMR (400 MHz, CDCl3); δ 7.12 (d, J = 7.8 Hz, 2H), 6.82 (d, J = 7.8 Hz, 2H), 3.78 (s, 3H), 2.79–2.75 (m, 2H), 2.56–2.49 (m, 6H), 1.46 (m, 4H), 1.25 (bs, 2H).
13C NMR (101 MHz, CDCl3); δ 157.82, 132.58, 129.57, 113.75, 61.64, 55.22, 54.51, 32.62, 25.90, 24.37.
- Catalytic intermolecular hydroaminations of unactivated olefins with secondary alkyl amines
- Anti-Markovnikov Hydroamination of Unactivated Alkenes with Primary Alkyl Amines
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