CAS RN: 12148-71-9 | Product Number: C2662
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|Molecular Formula / Molecular Weight||C__1__8H__3__0Ir__2O__2 = 662.87|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Light Sensitive,Air Sensitive,Moisture Sensitive,Heat Sensitive|
|Reaxys Registry Number||14520157|
|PubChem Substance ID||160871404|
|Appearance||Light yellow to Amber to Dark green powder to crystal|
|Elemental analysis(Carbon)||31.50 to 34.00 %|
|Melting Point||179 °C(dec.)|
Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent
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.
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