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CAS RN: 12148-71-9 | Product Number: C2662

(1,5-Cyclooctadiene)(methoxy)iridium(I) Dimer


Purity:
Synonyms:
  • Bis(1,5-cyclooctadiene)di-μ-methoxydiiridium(I)
Documents:
200MG
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1G
€540.00
1   ≥100 

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Product Number C2662
Molecular Formula / Molecular Weight C__1__8H__3__0Ir__2O__2 = 662.87 
Physical State (20 deg.C) Solid
Storage Temperature Frozen (<0°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Light Sensitive,Air Sensitive,Moisture Sensitive,Heat Sensitive
CAS RN 12148-71-9
Reaxys Registry Number 14520157
PubChem Substance ID 160871404
MDL Number

MFCD08459360

Specifications
Appearance Light yellow to Amber to Dark green powder to crystal
Elemental analysis(Carbon) 31.50 to 34.00 %
Properties (reference)
Melting Point 179 °C(dec.)
GHS
Related Laws:
Transport Information:
HS Number 2843909000
Application
TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst

TCI Practical Example: Hartwig-Miyaura C-H Borylation Using an Iridium Catalyst

Used Chemicals

Procedure

A solution of dtbpy (27 mg, 0.05 mmol), bis(pinacolato)diboron (1.0 g, 4.0 mmol) and [Ir(cod)OMe]2 (33 mg, 0.025 mmol) in cyclohexane (40 mL) was stirred under nitrogen at room temperature for 10 min. Benzo[1,2-b:4,5-b']dithiophene (380 mg, 2.0 mmol) was added the mixture and stirred 80 ˚C for 18 hours. The reaction mixture was quenched with water and separated both layers, extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the crude was washed with methanol (20 mL) to give 1 as a white solid (0.771 g, 87% yield).

Experimenter’s Comments

The reaction mixture was monitored by NMR.
Cyclohexane was bubbled with nitrogen before use.

Analytical Data

Compound 1

1H NMR (270 MHz, CDCl3); δ 8.36 (s, 2H), 7.90 (s, 2H), 1.39 (s, 24H).

Lead Reference


Application
Hartwig-Miyaura C-H Borylation

Reference


Application
Catalytic Functionalization of Un-activated Primary C―H Bonds

Typical Procedure:
An alcohol or ketone substrate is dissolved in THF and treated with a freshly prepared solution of [Ir(cod)OMe]2 (0.05 mol%) in THF and then with neat Et2SiH2 (1.2 eq.). The resulting solution is stirred at room temperature (23 °C) until complete conversion of the alcohol or ketone. At the completion of the reaction, the corresponding diethyl(hydrido)silyl ether is observed. Then the reaction mixture is placed under high vacuum for 1 h. The concentrated diethyl(hydrido)silyl ether is sequentially treated with freshly prepared solutions of norbornene (1.2 eq.) in THF and [Ir(cod)OMe]2 (0.5 mol%) in THF, and then with a slurry of Me4phen (1.25 mol%) in THF. The resulting solution is stirred at room temperature for 1 h and then heated it at 80-120 °C until complete conversion to the corresponding oxasilolane is observed. Then the crude reaction mixture containing the oxasilolane is sequentially treated with MeOH, KHCO3 (2.5 eq.) and H2O2 (30% solution in H2O, 10 eq.), and the resulting mixture is stirred overnight at 50 °C. The reaction is carefully quenched with aq. NaHSO3, and the resulting mixture is extracted with EtOAc. The combined organic layer is sequentially washed with 1 M HCl and sat. NaHCO3, and then dried with MgSO4. The resulting organic layer is filtered through Celite and concentrated to provide the crude diol, which is either purified directly or after conversion to the corresponding acetate derivative through treatment with Ac2O and Et3N.

References


PubMed Literature


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