12148-71-9 Usage
Description
DI-MU-METHOXOBIS(1,5-CYCLOOCTADIENE)DIIRIDIUM(I), also known as methoxy(cyclooctadiene)iridium(I) dimer, is a yellow solid catalyst with significant applications in various chemical reactions. It is particularly known for its role in the preparation of heteroaryl fused indole ring systems, inhibition of HCV NS5B polymerase, borylation, and Suzuki-Miyaura coupling. Additionally, it is utilized in tetraborylation reactions and ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives through C-H activation. One of its most notable uses is in highly regio and enantioselective asymmetric hydroboration, making it a valuable catalyst in the field of organic chemistry.
Uses
Used in Pharmaceutical Industry:
DI-MU-METHOXOBIS(1,5-CYCLOOCTADIENE)DIIRIDIUM(I) is used as a catalyst for the preparation of heteroaryl fused indole ring systems, which are essential in the development of new pharmaceutical compounds. Its ability to inhibit HCV NS5B polymerase makes it a potential candidate for the treatment of hepatitis C virus.
Used in Chemical Synthesis:
In the field of chemical synthesis, DI-MU-METHOXOBIS(1,5-CYCLOOCTADIENE)DIIRIDIUM(I) is used as a catalyst for borylation and Suzuki-Miyaura coupling reactions. These reactions are crucial for the formation of carbon-carbon and carbon-heteroatom bonds, which are fundamental in the synthesis of various organic compounds.
Used in C-H Activation:
DI-MU-METHOXOBIS(1,5-CYCLOOCTADIENE)DIIRIDIUM(I) is employed as a powerful C-H activation catalyst to prepare phenols from arenes. This application is significant in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and materials.
Used in Asymmetric Hydroboration:
The catalyst is used in highly regio and enantioselective asymmetric hydroboration, a reaction that plays a vital role in the synthesis of enantiomerically pure compounds. This application is particularly important in the pharmaceutical industry, where the development of single-enantiomer drugs is increasingly preferred due to their improved safety and efficacy profiles.
Used in Material Science:
In the material science industry, DI-MU-METHOXOBIS(1,5-CYCLOOCTADIENE)DIIRIDIUM(I) is used as a catalyst for tetraborylation reactions and ortho-silylation of aryl ketone, benzaldehyde, and benzyl alcohol derivatives. These reactions contribute to the development of new materials with unique properties, such as improved thermal stability, electrical conductivity, or mechanical strength.
Check Digit Verification of cas no
The CAS Registry Mumber 12148-71-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,2,1,4 and 8 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 12148-71:
(7*1)+(6*2)+(5*1)+(4*4)+(3*8)+(2*7)+(1*1)=79
79 % 10 = 9
So 12148-71-9 is a valid CAS Registry Number.
InChI:InChI=1/2C8H12.2CH3O.4CH3.2Ir/c2*1-2-4-6-8-7-5-3-1;2*1-2;;;;;;/h2*1-2,7-8H,3-6H2;2*1H3;4*1H3;;/b2*2-1-,8-7-;;;;;;;;/r2C8H12.C6H18Ir2O2/c2*1-2-4-6-8-7-5-3-1;1-7(2)9(5)8(3,4)10(7)6/h2*1-2,7-8H,3-6H2;1-6H3/b2*2-1-,8-7-;
12148-71-9Relevant articles and documents
Formation and reactivity of an (alkene)peroxoiridium(iii) intermediate supported by an amidinato ligand
Kelley, Matthew R.,Rohde, Jan-Uwe
, p. 527 - 537 (2014)
An IrI complex of an acetamidinato ligand was synthesized by reaction of N,N′-diphenylacetamidine, PhNC(Me)NHPh, with either MeLi and [{Ir(cod)}2(μ-Cl)2] or [{Ir(cod)}2(μ-OMe) 2] and was characterized by X-ray crystallography as a mononuclear complex, [Ir{PhNC(Me)NPh}(cod)] (1; where cod = 1,5-cyclooctadiene). Reaction of 1 with CO afforded a dinuclear carbonyl complex, [{Ir(CO)2} 2{μ-PhNC(Me)NPh-κN:κN′}2] (2), as indicated by EI mass spectrometry and solution- and solid-state IR spectroscopy [νCO (n-pentane) = 2067, 2034 and 1992 cm-1]. Activation of O2 by 1 in solution at 20°C was irreversible and produced an (alkene)peroxoiridium(iii) intermediate, [Ir{PhNC(Me)NPh}(cod) (O2)] (3), which was characterized by one- and two-dimensional NMR techniques and IR spectroscopy (for 3, νOO = 860 cm-1; for 3-18O2, νOO = 807 cm-1). Complex 3 oxidized PPh3 to OPPh3, and its decay in the absence of added substrates followed by reaction with cod yielded 4-cycloocten-1-one and a minor amount of 1. In comparison with the results for the previously reported guanidinato complex [Ir{PhNC(NMe2)NPh}(cod) (O2)] (4), the formation of 3 and its reaction with PPh3 are significantly faster, indicating considerable ligand effects in these reactions.
Process for the synthesis of phenols from arenes
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Page 15-16, (2008/06/13)
A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.
